Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Thirty Six Years of Research on the Selective Reduction and Hydroboration

  • Received : 2011.02.24
  • Accepted : 2011.03.09
  • Published : 2011.06.20
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Abstract

From 1975 to 2011, for thirty six years, the author and his collaborators have developed a variety of reducing and hydroborating agents, and applied them to organic synthesis, which involves the 1,2-reduction of ${\alpha}$,${\beta}$-unsaturated carbonyl compounds, stereoselective reduction of cycloalkanones, regioselective ring-opening of epoxides, partial reduction of carboxylic acid derivatives to aldehydes, regioselective addition to carbon-carbon multiple bonds, etc. by utilizing metal hydrides and the newly-devised the Meerwein-Ponndorf-Verley (MPV) type reagents. Such developments provide a new synthetic methodology making possible valuable selective reductions and hydroborations, not practical previously.

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References

  1. Yoon, N. M.; Cha, J. S. J. Korean Chem. Soc. 1977, 21, 108.
  2. Brown, H. C.; Krishnamurthy, S. Tetrahedron 1979, 35, 567. https://doi.org/10.1016/0040-4020(79)87003-9
  3. Brown, H. C.; Schlesinger, H. I.; Burg, A. B. J. Am. Chem. Soc. 1939, 61, 673. https://doi.org/10.1021/ja01872a041
  4. Kim, J. D.; Park, B. S.; Cha, J. S. J. Natural Sciences 1981, 1, 101.
  5. Yoon, N. M.; Oh, I. H.; Choi, K. I.; Lee, H. J. Heterocycles 1984, 22, 39. https://doi.org/10.3987/R-1984-01-0039
  6. Yoon, N. M.; Cha, J. S.; Park, W. S. Bull. Korean Chem. Soc. 1983, 4, 14.
  7. Yoon, N. M.; Cha, J. S. J. Korean Chem. Soc. 1978, 22, 37.
  8. Yoon, N. M.; Cha, J. S. J. Korean Chem. Soc. 1978, 22, 259.
  9. Cha, J. S.; Lee, J. C.; Kim, J. E.; Lee, K. W.; Yoon, M. S. Bull. Korean Chem. Soc. 1987, 8, 304.
  10. Cha, J. S.; Kim, J. M.; Lee, J. C.; Lee, H. S. Bull. Korean Chem. Soc. 1991, 12, 612.
  11. Brown, H. C.; Cha, J. S.; Nazer, B.; Yoon, N. M. J. Am. Chem. Soc. 1984, 106, 8001. https://doi.org/10.1021/ja00337a075
  12. Brown, H. C.; Cha, J. S.; Yoon, N. M.; Nazer, B. J. Org. Chem. 1987, 52, 5400. https://doi.org/10.1021/jo00233a018
  13. Brown, H. C.; Nazer, B.; Cha, J. S.; Sikorski, J. A. J. Org. Chem. 1986, 51, 5264. https://doi.org/10.1021/jo00376a040
  14. Cha, J. S.; Kim, J. E.; Kim, J. D. Tetrahedron Lett. 1985, 26, 6453. https://doi.org/10.1016/S0040-4039(00)99025-7
  15. Cha, J. S.; Kim, J. E.; Oh, S. Y. Bull. Korean Chem. Soc. 1987, 8, 313.
  16. Cha, J. S.; Kim J. E.; Oh, S. Y.; Lee, J. C.; Lee, K. W. Tetrahedron Lett. 1987, 28, 2389. https://doi.org/10.1016/S0040-4039(00)96132-X
  17. Cha, J. S.; Kim, J. E.; Lee, K. W. J. Org. Chem. 1987, 52, 5030. https://doi.org/10.1021/jo00231a037
  18. Cha, J. S.; Oh, S. Y.; Kim, J. E. Bull. Korean Chem. Soc. 1987, 8, 301.
  19. Cha, J. S.; Lee, K. W.; Yoon, M. S.; Lee, J. C. Bull. Korean Chem. Soc. 1988, 9, 384.
  20. Cha, J. S.; Brown, H. C. Bull. Korean Chem. Soc. 2005, 26, 292. https://doi.org/10.5012/bkcs.2005.26.2.292
  21. Cha, J. S.; Min, S. J.; Kim, J. M. Bull. Korean Chem. Soc. 1994, 15, 478.
  22. Cha, J. S.; Min S. J.; Kim, J. M.; Kwon, O. O.; Jeoung, M. K. Org. Prep. Proced. Int. 1993, 25, 466. https://doi.org/10.1080/00304949309457991
  23. Cha, J. S.; Min, S. J.; Kim, J. M.; Kwon, O. O.; Kim, E. J. Bull. Korean Chem. Soc. 1995, 16. 37.
  24. Cha, J. S.; Chang, S. W.; Kim, J. M.; Kwon, O. O.; Chun, J. H.; Cho, S. D.; Lee, H. S. Org. Prep. Proced. Int. 1998, 30, 63. https://doi.org/10.1080/00304949809355260
  25. Cha, J. S.; Chang, S. W.; Kim, J. M.; Kwon, O. O.; Chun, J. H.; Cho, S. D. Bull. Korean Chem. Soc. 1998, 19, 243.
  26. Cha, J. S.; Chang, S. W.; Kim, J. M.; Know, O. O.; Lee, J. C. Org. Prep. Proced. Int. 1997, 29, 665. https://doi.org/10.1080/00304949709355246
  27. Brown, H. C.; Cha, J. S.; Nazer, B. Inorg. Chem. 1984, 23, 2929. https://doi.org/10.1021/ic00187a006
  28. Brown, H. C.; Cha, J. S.; Nazer, B.; Kim, S.-J.; Krishnamurthy, S. J. Org. Chem. 1984, 49, 885. https://doi.org/10.1021/jo00179a026
  29. Brown, H. C.; Nazer, B.; Cha, J. S. Synthesis 1984, 498.
  30. Cha, J. S.; Kim, J. E.; Lee, J. C.; Yoon, M. S. Bull. Korean Chem. Soc. 1986, 7, 66.
  31. Brown, H. C.; Cha, J. S.; Nazer, B. J. Org. Chem. 1985, 50, 549. https://doi.org/10.1021/jo00205a001
  32. Brown, H. C.; Cha, J. S.; Nazer, B. J. Org. Chem. 1984, 49, 2073. https://doi.org/10.1021/jo00185a067
  33. Cha, J. S.; Yoon, M. S.; Lee, K. W.; Lee, J. C. Heterocycles 1988, 27, 1455. https://doi.org/10.3987/COM-88-4549
  34. Cha, J. S.; Yoon, M. S.; Kim, Y. S.; Lee, K. W. Tetrahedron Lett. 1988, 29, 1069. https://doi.org/10.1016/0040-4039(88)85337-1
  35. Cha, J. S.; Yoon, M. S.; Lee, K. W.; Lee, J. C. Bull. Korean Chem. Soc. 1989, 10, 75.
  36. Cha, J. S.; Yoon, M. S. Tetrahedron Lett. 1989, 30, 3677. https://doi.org/10.1016/S0040-4039(01)80481-0
  37. Brown, H. C.; Park, W. S.; Cha, J. S.; Cho, B. T. J. Org. Chem. 1986, 51, 337. https://doi.org/10.1021/jo00353a012
  38. Cha, J. S.; Lee, S. E. Bull. Korean Chem. Soc. 1992, 13, 531.
  39. Cha, J. S.; Lee, D. Y. Bull. Korean Chem. Soc. 2002, 23, 856. https://doi.org/10.5012/bkcs.2002.23.6.856
  40. Cha, J. S.; Lee, D. Y.; Moon, S. J. Bull. Korean Chem. Soc. 2001, 22, 661.
  41. Cho, S. D.; Lim, H. J.; Kim, H. J.; Cha, J. S. Bull. Korean Chem. Soc. 2002, 23, 1695. https://doi.org/10.5012/bkcs.2002.23.12.1695
  42. Cha, J. S.; Brown, H. C. J. Org. Chem. 1993, 58, 4727. https://doi.org/10.1021/jo00069a042
  43. Cha, J. S.; Brown, H. C. Org. Prep. Proced. Int. 1994, 26, 459. https://doi.org/10.1080/00304949409458036
  44. Cha, J. S.; Brown, H. C. J. Org. Chem. 1993, 58, 4732. https://doi.org/10.1021/jo00069a043
  45. Cha, J. S.; Kwon, S. Y.; Kim, J. M.; Kwon, O. O.; Lee, K. W. Bull. Korean Chem. Soc. 1999, 20, 737.
  46. Cha, J. S.; Yu, S. J.; Roh, M. Y.; Yi, J. E.; Park, S. J.; Kwon, O. O. Bull. Korean Chem. Soc. 2008, 29, 2379. https://doi.org/10.5012/bkcs.2008.29.12.2379
  47. Cha, J. S.; Yu, S. J. Bull. Korean Chem. Soc. 2009, 30, 1588. https://doi.org/10.5012/bkcs.2009.30.7.1588
  48. Brown, H. C.; Yoon, N. M. J. Am. Chem. Soc. 1966, 88, 1484.
  49. Yoon, N. M.; Brown, H. C. J. Am. Chem. Soc. 1968, 90, 2927. https://doi.org/10.1021/ja01013a033
  50. Cha, J. S.; Brown, H. C. J. Org. Chem. 1993, 58, 3974. https://doi.org/10.1021/jo00067a033
  51. Cha, J. S.; Kwon, O. O.; Kim, J. M. Bull. Korean Chem. Soc. 1994, 15, 132.
  52. Cha, J. F.; Kwon, O. O.; Lee, J. C.; Kim, J. M. Bull. Korean Chem. Soc. 1994, 15, 644.
  53. Cha, J. S.; Lee, K. D.; Kwon, O. O.; Kim, J. M.; Lee, H. S. Bull. Korean Chem. Soc. 1995, 16, 561.
  54. Cha, J. S.; Moon, S. J. Bull. Korean Chem. Soc. 2002, 23, 1340. https://doi.org/10.5012/bkcs.2002.23.9.1340
  55. Yoon, N. M.; Gyoung, Y. S. J. Org. Chem. 1985, 50, 2443. https://doi.org/10.1021/jo00214a009
  56. Cha, J. S.; Jeong, M. K.; Kwon, O. O.; Lee, K. D.; Lee, H. S. Bull. Korean Chem. Soc. 1994, 15, 873.
  57. Cha, J. S.; Kwon, O. O.; Jeoung, M. K.; Kim, E. J. Bull. Korean Chem. Soc. 1994, 15, 1021.
  58. Cha, J. S.; Chang, S. W.; Kwon, O. O.; Kim, J. M. Synlett 1996, 165.
  59. Cha, J. S.; Chang, S. W.; Lee, J. E.; Kim, J. M.; Kwon, O. O.; Lee, H. S.; Song, H. C. Bull. Korean Chem. Soc. 1996, 17, 720.
  60. Cha, J. S.; Lee, J. C.; Kim, J. M.; Jeong, S. W.; Park, K. S.; Lee, S. E.; Lee, H. S. Bull. Korean Chem. Soc. 1992, 13, 581.
  61. Cha, J. S.; Lee, J. C. Bull. Korean Chem. Soc. 1993, 14, 469.
  62. Cha, J. S.; Lee, S. E.; Lee, H. S. Bull. Korean Chem. Soc. 1991, 12, 644.
  63. Cha, J. S.; Kwon, O. O.; Lee, J. C. Bull. Korean Chem. Soc. 1993, 14, 743.
  64. Cha, J. S.; Lee, J. C.; Ju, Y. C. Bull. Korean Chem. Soc. 1997, 18, 890.
  65. Cha, J. S.; Min, S. J.; Lee, J. C.; Lee, H. S.; Lee, S. E. Org. Prep. Proced. Int. 1992, 24, 335. https://doi.org/10.1080/00304949209355895
  66. Cha, J. S. Bull. Korean Chem. Soc. 1992, 13, 670.
  67. Cha, J. S.; Lee, J. C.; Lee, J. C.; Lee, H. S.; Lee, S. E.; Kim, J. M.; Kwon, O. O.; Min, S. J. Tetrahedron Lett. 1991, 32, 6903. https://doi.org/10.1016/0040-4039(91)80439-D
  68. Cha, J. S.; Lee, J. C.; Lee, H. S.; Lee, S. E. Bull. Korean Chem. Soc. 1991, 12, 598.
  69. Cha, J. S.; Lee, S. E. Bull. Korean Chem. Soc. 1992, 13, 451,
  70. Cha, J. S.; Lee, S. E.; Lee, H. S. Org. Prep. Proced. Int. 1992, 24, 331. https://doi.org/10.1080/00304949209355894
  71. Cha, J. S.; Kim, J. M.; Jeoung, M. K; Lee, K. D. Bull. Korean Chem. Soc. 1992, 13, 702.
  72. Cha, J. S.; Jeoung, M. K.; Kim, J. M.; Kwon, O. O.; Lee, K. D.; Kim, E. J. Bull. Korean Chem. Soc. 1994, 15, 881.
  73. Cha, J. S.; Kim, J. M.; Jeoung, M. K.; Kwon, O. O.; Kim, E. J. Org. Prep. Proced. Int. 1995, 27, 95. https://doi.org/10.1080/00304949509458184
  74. Cha, J. S.; Kim, J. M.; Jeoung, M. K. Bull. Korean Chem. Soc. 1994, 15, 708.
  75. Cha, J. S.; Jeoung, M. K.; Kim, J. M.; Kwon, O. O.; Lee, J. C. Org. Prep. Proced. Int. 1994, 26, 583. https://doi.org/10.1080/00304949409458063
  76. Cha, J. S.; Jang, S. H.; Kwon, S. Y. Bull. Korean Chem. Soc. 2002, 23, 1695. https://doi.org/10.5012/bkcs.2002.23.12.1695
  77. Cha, J. S.; Jang, S. H.; Park, J. H.; Kim, S. K.; Lee, C. S.; Lee, Y. R. Bull. Korean Chem. Soc. 2003, 24, 9. https://doi.org/10.5012/bkcs.2003.24.1.009
  78. Cha, J. S.; Yu, S. J. J. Incl. Phenom. Macrocycl. Chem. 2009, 65, 7. https://doi.org/10.1007/s10847-009-9628-4
  79. Cha, J. S.; Kim, J. E.; Yoon, M. S.; Kim, Y. S. Tetrahedron Lett. 1987, 28, 6231. https://doi.org/10.1016/S0040-4039(00)61855-5
  80. Cha, J. S.; Kim, J. E.; Oh, S. Y.; Kim, J. D. Tetrahedron Lett. 1987, 28, 4575. https://doi.org/10.1016/S0040-4039(00)96568-7
  81. Cha, J. S.; Oh, S. Y.; Lee, K. W.; Yoon, M. S.; Lee, J. C.; Kim, J. E. Bull. Korean Chem. Soc. 1988, 9, 48.
  82. Cha, J. S.; Lee, J. C.; Yoon, M. S.; Seo, J. B.; Kim, J. M. Bull. Korean Chem. Soc. 1987, 11, 76.
  83. Cha, J. S.; Lee, J. C.; Lee, H. S.; Lee, S. E. Org. Prep. Proced. Int. 1992, 24, 285.
  84. Brown, H. C.; Kulkarni, S. V.; Rao, C. G. Synthesis 1979, 702.
  85. Cha, J. S.; Kim, M.-G.; Kim, J. M.; Kwon, O. O.; Chun, J. H.; Cho, S. D. Bull. Korean Chem. Soc. 1998, 19, 724.
  86. Cha, J. S.; Kim, J. M.; Chun, J. H.; Kwon, O. O.; Lee, J. C. Bull. Korean Chem. Soc. 1998, 19, 730.
  87. Cha, J. S.; Chun, J. H.; Kim, J. M.; Kwon, O. O.; Kwon, S. Y.; Lee, J. C. Bull. Korean Chem. Soc. 1999, 20, 400.
  88. Cha, J. S.; Lee, D. Y.; Kim, J. M. Org. Prep. Proced. Int. 1999, 31, 694. https://doi.org/10.1080/00304949909355352
  89. Cha, J. S.; Oh, S. Y.; Lee, K. W.; Yoon, M. S.; Lee, J. C. Heterocycles 1988, 27, 1595. https://doi.org/10.3987/COM-88-4570
  90. Cha, J. S.; Lee, K. W.; Yoon, M. S.; Lee, J. C. Bull. Korean Chem. Soc. 1988, 9, 384.
  91. Cha, J. S.; Park, J. H.; Lee, D. Y. Bull. Korean Chem. Soc. 2001, 22, 325.
  92. Cha, J. S.; Park, J. H.; Moon, S. J. Bull. Korean Chem. Soc. 2001, 22, 1089.
  93. Cha, J. S.; Kim, J. M.; Chun, J. H.; Kwon, O. O.; Kwon, S. Y.; Han, S. W. Org. Prep. Proced. Int. 1999, 31, 204. https://doi.org/10.1080/00304949909355712
  94. Cha, J. S.; Chun, J. H. Bull. Korean Chem. Soc. 1999, 20, 375.
  95. Cha, J. S.; Lee, D. Y. Bull. Korean Chem. Soc. 2000, 21, 1260.
  96. Cha, J. S.; Kim, J. M.; Chun, J. H.; Kwon, O. O.; Kwon, S. Y.; Cho, S. D. Bull. Korean Chem. Soc. 1998, 19, 1301.
  97. Cha, J. S.; Chun, J. H.; Kim, J. M.; Lee, D. Y.; Cho, S. D. Bull. Korean Chem. Soc. 1999, 20, 1373.
  98. Cha, J. S.; Lee, S. E.; Lee, H. S.; Lee, J. C.; Kim, J. M.; Kwon, O. O.; Min, S. J. Bull. Korean Chem. Soc. 1992, 13, 338.
  99. Cha, J. S. Org. Prep. Proced. Int. 1989, 21, 451. https://doi.org/10.1080/00304948909356413
  100. Cha, J. S. Org. Proc. Res. Devel. 2006, 10, 1032. https://doi.org/10.1021/op068002c
  101. Cha, J. S. Bull. Korean Chem. Soc. 2007, 28, 2162. https://doi.org/10.5012/bkcs.2007.28.12.2162
  102. Schlesinger, H. I.; Brown, H. C.; Hoekstra, H. R.; Rapp, L. R. J. Am. Chem. Soc. 1953, 75, 199. https://doi.org/10.1021/ja01097a053
  103. Finholt, A. E.; Bond, A. C., Jr.; Schlesinger, H. I. J. Am. Chem. Soc. 1947, 69, 1199. https://doi.org/10.1021/ja01197a061
  104. Verley, A. Bull. Soc. Chim. Fr. 1925, 37, 537, 871.
  105. Verley, A. Bull. Soc. Chim. Fr. 1927, 41, 788.
  106. Meerwein, H.; Schmidt, R. Liebigs Ann. 1925, 444, 221. https://doi.org/10.1002/jlac.19254440112
  107. Ponndorf, W. Z. Angew. Chem. 1926, 39, 138. https://doi.org/10.1002/ange.19260390504
  108. Lund, H. Dtsch. Chem. Ges. 1937, 70, 1520. https://doi.org/10.1002/cber.19370700713
  109. Meerwein, H.; Hinz, G.; Majert, H.; Sonke, H. J. Prakt. Chem. 1936, 147, 226. https://doi.org/10.1002/prac.19361470608
  110. Ziegler, K.; Schneider, K. Justus Liebigs Ann. Chem. 1959, 623, 9. https://doi.org/10.1002/jlac.19596230103
  111. Ziegler, K.; Schneider, K.; Schneider, J. Angew. Chem. 1955, 67, 425.
  112. Haeck, H. H.; Kralt, T. Rec. Trav. Chim. Pays-Bas 1966, 85, 343.
  113. Mikhailov, B. M.; Kiselev, V. G.; Bubnov, Y. N. Izv. AN SSSR, Ser. Khim. 1965, 898.
  114. Mikhailov, B. M.; Bubnov, Y. N.; Kiselev, V. G. Zh. Obsh. Khim. 1965, 36, 62
  115. Mikhailov, B. M.; Bubnov, Y. N.; Kiselev, V. G. J. Gen. Chem. USSR 1966, 36, 65.
  116. Midland, M. M.; Tramontano, A.; Zderic, S. A. J. Organometal. Chem. 1977, 134, C17. https://doi.org/10.1016/S0022-328X(00)93625-8
  117. Midland, M. M.; Tramontano, A.; Zderic, S. A. 1978, 156, 203. https://doi.org/10.1016/S0022-328X(00)84877-9
  118. Midland, M. M.; Tramontano, A. J. Org. Chem. 1978, 43, 1470. https://doi.org/10.1021/jo00401a043
  119. Chandrasekharan, J.; Ramachandran, P. V.; Brown, H. C. J. Org. Chem. 1985, 50, 5446. https://doi.org/10.1021/jo00225a109
  120. Brown, H. C.; Ramachandran, P. V.; Chandrasekharan, Heteroatom Chem. 1995, 6, 117. https://doi.org/10.1002/hc.520060206
  121. Cha, J. S.; Kwon, O. O.; Kwon, S. Y.; Kim, J. M.; Seo, W. W.; Chang, S. W. Synlett 1995, 1055.
  122. Cha, J. S.; Kwon, O. O.; Kwon, S. Y. Bull. Korean Chem. Soc. 1995, 16, 1009.
  123. Cha, J. S.; Park, S. J.; Yu, S. J.; Kim, S. K.; Kwon, O. O. Bull. Korean Chem. Soc. 2008, 29, 301. https://doi.org/10.5012/bkcs.2008.29.2.301
  124. Cha, J. S.; Park, S. J; Yu, S. J.; Kim, S. K.; Kwon, O. O. Bull. Korean Chem. Soc. 2008, 29, 301. https://doi.org/10.5012/bkcs.2008.29.2.301
  125. Cha, J. S.; Park, S. J. J. Chosun Natural Science 2009, 2, 185.
  126. Cha, J. S.; Kwon, O. O.; Kwon, S. Y. Org. Prep. Proced. Int. 1996, 28, 355. https://doi.org/10.1080/00304949609356544
  127. Cha, J. S.; Kwon, O. O. J. Org. Chem. 1997, 62, 3019. https://doi.org/10.1021/jo970083a
  128. Cha, J. S.; Kwon, O. O. Bull. Korean Chem. Soc. 1997, 18, 689.
  129. Cha, J. S.; Kwon, O. O.; Kim, J. M.; Chun J. H.; Lee, Y. S.; Lee, H. S.; Cho, S. D. Bull. Korean Chem. Soc. 1998, 19, 236.
  130. Cha, J. S.; Kwon, S. Y.; Kwon, O. O.; Kim, J. M.; Song, H. C. Bull. Korean Chem. Soc. 1996, 17, 900.
  131. Kwon, O. O.; Cha, J. S. Bull. Korean Chem. Soc. 2000, 21, 659.
  132. Cha, J. S.; Lee, K. W. J. Natural Sciences 2002, 22, 53.
  133. Cha, J. S.; Yi, J. E. J. Incl. Phenom. Macrocycl. Chem. 2009, 65, 15. https://doi.org/10.1007/s10847-009-9629-3
  134. Cha, J. S.; Park, S. J. Bull. Korean Chem. Soc. 2009, 30, 2823. https://doi.org/10.5012/bkcs.2009.30.11.2823
  135. Cha, J. S.; No, M. Bull. Korean Chem. Soc. 2010, 31, 840. https://doi.org/10.5012/bkcs.2010.31.04.840
  136. Cha, J. S.; Park, S. J. Bull. Korean Chem. Soc. 2010, 31, 2135. https://doi.org/10.5012/bkcs.2010.31.8.2135
  137. Cha, J. S.; Bull. Korean Chem. Soc. 2011, 32, 219. https://doi.org/10.5012/bkcs.2011.32.1.219
  138. Brown, H. C.; Kramer, G. W.; Levy, A. B.; Midland, M. M. Organic Synthesis via Boranes; Wiley-Interscience: New York, 1975.
  139. Chandrasekharan, J.; Ramachandran, P. V.; Brown, H. C. J. Org. Chem. 1985, 50, 5446. https://doi.org/10.1021/jo00225a109
  140. Brown, H. C.; Park, W. S.; Cho, B. T.; Ramachandran, P. V. J. Org. Chem. 1987, 52, 5406. https://doi.org/10.1021/jo00233a019
  141. Brown, H. C.; Srebnik, M.; Ramachandran, P. V. J. Org. Chem. 1989, 54, 1577. https://doi.org/10.1021/jo00268a018
  142. Brown, H. C.; Ramachandran, P. V. J. Org. Chem. 1989, 54, 4504. https://doi.org/10.1021/jo00280a013
  143. Brown, H. C.; Ramachandran, P. V.; Chandrasekharan, J. Heteroatom Chem. 1995, 6, 117. https://doi.org/10.1002/hc.520060206
  144. Cha, J. S.; Kim, E. J.; Kwon, O. O.; Kim, J. M. Bull. Korean Chem. Soc. 1996, 17, 50.
  145. Cha, J. S.; Kwon, O. O.; Lee, K. W.; Kim, J. M. Bull. Korean Chem. Soc. 2005, 26, 652. https://doi.org/10.5012/bkcs.2005.26.4.652
  146. Cha, J. S.; Kim, E. J.; Kwon, O. O.; Kwon, S. Y.; Seo, W. W.; Chang, S. W. Org. Prep. Proced. Int. 1995, 27, 541. https://doi.org/10.1080/00304949509458495
  147. Cha, J. S.; Kim, E. J.; Kwon, O. O.; Kim, J. M. Bull. Korean Chem. Soc. 1995, 16, 691.
  148. Cha, J. S.; Kwon, O. O.; Kim, J. M. Bull. Korean Chem. Soc. 1996, 17, 725.
  149. Cha, J. S.; Jang, S. H.; Kwon, S. Y.; Kwon, O. O. Bull. Korean Chem. Soc. 2004, 25, 603. https://doi.org/10.5012/bkcs.2004.25.5.603
  150. Cha, J. S.; Nam, H. T.; Kwon, S. Y.; Park, S. J.; Kwon, O. O. Bull. Korean Chem. Soc. 2004, 25, 1948. https://doi.org/10.5012/bkcs.2004.25.12.1948
  151. Cha, J. S.; Nam, H. T.; Park, S. J.; Kwon, S. Y.; Kwon, O. O. Bull. Korean Chem. Soc. 2006, 27, 667. https://doi.org/10.5012/bkcs.2006.27.5.667
  152. Cha, J. S. Bull. Korean Chem. Soc. 2009, 30, 1658. https://doi.org/10.5012/bkcs.2009.30.7.1658
  153. Cha, J. S.; Park, J. H. Bull. Korean Chem. Soc. 2002, 23, 1051. https://doi.org/10.5012/bkcs.2002.23.8.1051
  154. Cha, J. S.; Park, J. H. Bull. Korean Chem. Soc. 2002, 23, 1377. https://doi.org/10.5012/bkcs.2002.23.10.1377
  155. Cha, J. S.; Yu, S. J.; Roh, M. Y.; Park, S. J.; Yi, J. E.; Kwon, O. O. Bull. Korean Chem. Soc. 2008, 29, 885. https://doi.org/10.5012/bkcs.2008.29.4.885
  156. Cha, J. S.; Park, S. J.; Kwon, O. O. Unpublished results.
  157. Cha, J. S.; Kwon, O. O.; Kwon, S. Y. Bull. Korean Chem. Soc. 1995, 16, 1009.
  158. Cha, J. S.; Kwon, O. O.; Kwon, S. Y. Org. Prep. Proced. Int. 1996, 28, 355. https://doi.org/10.1080/00304949609356544
  159. Cha, J. S.; Kwon, O. O.; Kim, J. M.; Chun, J. H.; Lee, Y. S.; Lee, H. S.; Cho, S. D. Bull. Korean Chem. Soc. 1998, 19, 236.
  160. Cha, J. S.; Kwon, S. Y; Kwon, O. O.; Kim, J. M.; Song, H. Bull. Korean Chem. Soc. 1996, 17, 900.
  161. Cha, J. S.; Nam, H. T.; Kwon, O. O. Unpublished results.
  162. Cha, J. S.; Kim, E. J.; Kwon, O. O.; Kim, J. M. Bull. Korean Chem. Soc. 1994, 15, 1033.
  163. Cha, J. S.; Nam, H. T.; Jang S. H.; Kwon, S. Y.; Park, S. J.; Kwon, O. O. Bull. Korean Chem. Soc. 2004, 25, 1948. https://doi.org/10.5012/bkcs.2004.25.12.1948
  164. Cha, J. S.; Nam, H. T.; Park, S. J.; Kwon, S. Y.; Kwon, O. O. Bull. Korean Chem. Soc. 2006, 27, 667. https://doi.org/10.5012/bkcs.2006.27.5.667
  165. Krishnamurthy, S.; Brown, H. C. J. Am. Chem. Soc. 1976, 98, 3383. https://doi.org/10.1021/ja00427a061
  166. Brown, H. C.; Cha, J. S.; Nazer, B. J. Org. Chem. 1984, 49, 2073. https://doi.org/10.1021/jo00185a067
  167. Brown, H. C.; Krishnamurthy, S. J. Am. Chem. Soc. 1972, 94, 7159. https://doi.org/10.1021/ja00775a053
  168. Corey, E. J.; Becker, K. B.; Varma, R. K. J. Am. Chem. Soc. 1972, 94, 8616. https://doi.org/10.1021/ja00779a074
  169. Corey, E. J.; Albonico, S. M.; Koelliker, U.; Schaaf, T. K.; Varma, R. K. J. Am. Chem. Soc. 1971, 93, 1491. https://doi.org/10.1021/ja00735a033
  170. Corey, E. J.; Varma, R. K. J. Am. Chem. Soc. 1971, 93, 7319. https://doi.org/10.1021/ja00755a036
  171. Brown, H. C.; Kramer, G. W.; Hubbard, J. L.; Krishnamurthy, S. J. Organomet. Chem. 1980, 188, 1. https://doi.org/10.1016/S0022-328X(00)83693-1
  172. Cha, J. S.; Min, S. J.; Kim, J. M.; Kwon, O. O.; Jeoung, M. K. Org. Prep. Proced. Int. 1993, 25, 444.
  173. Krishnamurthy, S. Aldrichimica Acta 1974, 7, 55.
  174. Brown, C. A.; Krishnamurthy, S. J. Organomet. Chem. 1978, 156, 111. https://doi.org/10.1016/S0022-328X(00)84869-X
  175. Brown, H. C.; Krishnamurthy, S. Tetrahedron 1979, 35, 567. https://doi.org/10.1016/0040-4020(79)87003-9
  176. Cha, J. S.; Kwon, O. O.; Lee, K. W.; Kim, J. M. Bull. Korean Chem. Soc. 2005, 26, 652. https://doi.org/10.5012/bkcs.2005.26.4.652
  177. Cha, J. S.; Kwon, O. O. J. Org. Chem. 1997, 62, 3019. https://doi.org/10.1021/jo970083a
  178. Cha, J. S.; Kwon, O. O. Bull. Korean Chem. Soc. 1997, 18, 689.
  179. Ashby, E. C.; Yu, S. H. J. Org. Chem. 1970, 35, 1034. https://doi.org/10.1021/jo00829a038
  180. Heinsohn, G. E.; Ashby, E. C. J. Org. Chem. 1973, 38, 4232. https://doi.org/10.1021/jo00964a004
  181. Winterfeldt, E. Synthesis 1975, 617.
  182. Kwon, O. O.; Cha, J. S. Bull. Korean Chem. Soc. 2000, 21, 659.
  183. Cha, J. S.; Kwon, O. O.; Kim, J. M.; Cha, S. D. Synlett 1997, 1465.
  184. Cha, J. S.; Moon, S. J.; Kwon, O. O.; Lee, Y. R. Bull. Korean Chem. Soc. 2000, 21, 128.
  185. Cha, J. S.; Moon, S. J.; Park, J. H. J. Org. Chem. 2001, 66, 7514. https://doi.org/10.1021/jo010401c
  186. Brown, H. C.; Weissman, P. M.; Yoon, N. M. J. Am. Chem. Soc. 1966, 88, 1458. https://doi.org/10.1021/ja00959a026
  187. Krishnamurthy, S.; Schubert, R. M.; Brown, H. C. J. Am. Chem. Soc. 1973, 95, 8486. https://doi.org/10.1021/ja00806a067
  188. Brown, H. C.; Heim, P.; Yoon, N. M. J. Am. Chem. Soc. 1970, 92, 1637. https://doi.org/10.1021/ja00709a037
  189. Brown, H. C.; Yoon, N. M. J. Am. Chem. Soc. 1966, 88, 1464. https://doi.org/10.1021/ja00959a027
  190. Yoon, N. M.; Brown, H. C. J. Am. Chem. Soc. 1968, 90, 2927. 147. https://doi.org/10.1021/ja01003a026
  191. Hutchins, R. O.; Taffer, I. M.; Burgoyne, W. J. Org. Chem. 1981, 46, 5214. https://doi.org/10.1021/jo00338a031
  192. Hutchins, R. O.; Taffer, I. M.; Burgoyne, W. J. Org. Chem. 1981, 46, 5214. https://doi.org/10.1021/jo00338a031
  193. Yoon, N. M.; Kim, K. E. J. Org. Chem. 1987, 52, 5564. https://doi.org/10.1021/jo00234a011
  194. Brown, H. C.; Yoon, N. M. Chem. Commun. 1968, 1549.
  195. Cha, J. S.; Park, J. H. Bull. Korean Chem. Soc. 2002, 23, 1377. https://doi.org/10.5012/bkcs.2002.23.10.1377
  196. Cha, J. S.; Yu, S. J.; Roh, M. Y.; Park, S. J.; Yi, E. J.; Kwon, O. O. Bull Korean Chem. Soc. 2009, 29, 885. https://doi.org/10.5012/bkcs.2008.29.4.885
  197. Kim, J. D.; Kim, J. E.; Cha, J. S. Bull. Korean Chem. Soc. 1982, 3, 130.
  198. Park, W. S.; Cho, B. T.; Cha, J. S. Bull. Korean Chem. Soc. 1987, 8, 10.
  199. Yoon, M. N.; Cha, J. S. Unpublished results.
  200. Cha, J. S.; Min, S. J.; Kim, J. M.; Kwon, O. O. Tetrahedron Lett. 1993, 34, 5113. https://doi.org/10.1016/S0040-4039(00)60690-1
  201. Cha, J. S.; Min, S. J.; Kim, J. M.; Kwon, O. O.; Kim, E. J. Bull. Korean Chem. Soc. 1994, 15, 687.
  202. Cha, J. S.; Seo, W. W.; Kim, J. M.; Kwon, O. O. Bull. Korean Chem. Soc. 1996, 17, 892.

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