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Reaction of Lithium (2,3-Dimethyl-2-butyl)-t-butoxyborohydride with Selected Organic Compounds Containing Representative Functional Groups


Abstract

The general reducing charagteristics of a newly synthesized reducing agent, lithium(2.3-dimethyl-2-butyl)-${\iota}$-butoxyborohydride (Li $Thx'BuOB_2$, 1), in tetrahydrofuran (THF) toward selected organic compounds containing representative fundtional groups under practical has been examined. The reagent revealed an interesting and unique reducing characteristics. Especially, the stereoselectivity in the reduction of cyclic ketones was extraordinary. Thus, the introduction of bulky alkyl and alkoxy groups into the parent borohydride affonds a high stereoselectivity. In general, the reducing power of the reagent is somewhere between the dialiylborohydride and the parent borohydride. This permits the reagent to be a reagent of choice for selecitive reduction of organic compounds with an improved selectivity.

Keywords

References

  1. Yoon, N. M; Cha, J. S. J. Korean Chem. Soc. 1977, 21, 108.
  2. Krishnamurthy, S. Aldrichmica Acta 1974, 7, 55.
  3. Krishnamurthy, S.; Brown, H. C. J. Am. Chem. Soc. 1976, 98, 3383. https://doi.org/10.1021/ja00427a061
  4. Krishnamurthy, S.; Brown, H. C. J. Org. Chem. 1976, 41, 3064. https://doi.org/10.1021/jo00880a045
  5. Brown, H. C; Kim, S. C. Synthesis 1977, 635.
  6. Brown, H. C; Mathew, C. P.; Pyun, C; Son, J. C; Yoon, N. M. J. Org. Chem. 1984, 49,3091. https://doi.org/10.1021/jo00191a010
  7. Cha, J. S.; Kim, J. E.; Lee, J. C; Yoon, M. S. Bull. Korean Chem. Soc. 1986, 7, 66.
  8. Brown, H. C; Moerikofer, A. W. J. Am. Chem. Soc. 1962, 84, 1478. https://doi.org/10.1021/ja00867a024
  9. Brown, H. C; Klender, G. J. Inorg Chem. 1962,1, 204. https://doi.org/10.1021/ic50002a003
  10. Brown, H. C; Heim, P.; Yoon, N. M. J. Org. Chem. 1972, 37, 2942. https://doi.org/10.1021/jo00984a006
  11. Corey, E. J.; Becker, K. B.; Varma, R. K. J. Am. Chem. Soc. 1972, 94, 8616. https://doi.org/10.1021/ja00779a074
  12. 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
  13. Corey, E. J.; Varma, R. K. J. Am. Chem. Soc. 1971, 93, 7319. https://doi.org/10.1021/ja00755a036
  14. 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
  15. Brown, H. C; Cha, J. S.; Nazer, B. J. Org. Chem. 1984, 49, 2073. https://doi.org/10.1021/jo00185a067
  16. Cha, J. S.; Yoon, M. S.; Lee, K. W.; Lee, J. C. Heterocycles 1988, 27, 1455. https://doi.org/10.3987/COM-88-4549
  17. Brown, H. C; Krishnamurthy, S. J. Am. Chem. Soc. 1972, 94, 7159. https://doi.org/10.1021/ja00775a053
  18. Brown, H. C; Kramer, G. W.; Levy, A. B.; Midland, M. M. Organic Synthesis via Boranes; Wiley-Interscience: New York, 1975.
  19. Organic Synthesis via Boranes Brown, H. C.;Kramer, G. W.;Levy, A. B.;Midland, M. M.

Cited by

  1. ChemInform Abstract: Reaction of Lithium (2,3-Dimethyl-2-butyl)-t-butoxyborohydride with Selected Organic Compounds Containing Representative Functional Groups. vol.33, pp.45, 2010, https://doi.org/10.1002/chin.200245043
  2. Thirty Six Years of Research on the Selective Reduction and Hydroboration vol.32, pp.6, 2011, https://doi.org/10.5012/bkcs.2011.32.6.1808