DOI QR코드

DOI QR Code

Transformation of Bicyclic Ketal Compound to 1,2-Cyclopentanediol via 1,5-Diketone

  • 발행 : 1992.04.20

초록

New method for preparing cyclopentanediol from bicyclic ketal is described. Bicyclic ketal is cleaved to give 1,5-diketone, which is then reductively coupled intramolecularly to yield 1,2-cyclopentanediol. A solution of bicyclic ketal (1a) in methylene chloride was treated with aluminum chloride(2 eq.)-sodium iodide(l.5 eq.) at ambient temperature for 3 h to give the 1,5-diketone (2a) in 71% yield after basic work-up followed by short path column chromatography. A solution of the 1,5-diketone (2a) in THF was reacted with titanium tetrachloride(6 eq.)-Mg(Hg)(0.3 eq.) at $0^{\circ}C$ for 4 h to give the 1,2-cyclopentanediol (3a) in 75% yield after basic work-up followed by short path column chromatography.

키워드

참고문헌

  1. Tetrahedron v.37 no.25 L. A. Paquette(ed.)
  2. Topic in Current Chemistry v.79 L. A. Paquette
  3. J. Chem. Soc. Perkin Trans. 1 J.-G. Jun;D. G. Shin
  4. Bull. Korean Chem. Soc. v.11 no.4 J.-G. Jun;D. G. Shin;C. K. Lee;K. S. Sin
  5. Bull. Korean Chem. Soc. v.9 no.3 J.-G. Jun;B. P. Mundy
  6. J. Chem. Soc. Perkin Trans. 1 J.-G. Jun;S. Suh;D. G. Shin
  7. J. Am. Chem. Soc. v.96 J. E. McMurry;M. P. Fleming
  8. J. Org. Chem. v.41 E. J. Corey;R. L. Danheiser;S. Chandrasekaran
  9. Chem. Lett. T. Mukaiyama;T. Sato;J. Hanna
  10. Heterocycles v.6 B. P. Mundy;K. B. Lipkowitz;G. W. Dirks
  11. Tetrahedron Lett. v.26 B. P. Mundy;M. Bjorklund
  12. Tetrahedron Lett. v.26 M. Bjorklund;J.-G. Jun;B. P. Mundy
  13. Chem. Lett. H. Kotsuki;Y. Ushio;I. Kadata;M. Ochi
  14. Tetrahedron Lett. v.28 K. Ishihara;A. Mori;H. Yamamoto
  15. J. Org. Chem. v.46 B. P. Mundy;G. W. Dirks;R. M. Larter;A. C. Craig;K. B. Lipkowitz;J. Carter
  16. Synthesis D. Lenoir
  17. Tetrahedron Lett. v.30 J. E. McMurry;J. G. Rico
  18. J. Org. Chem. v.41 J. E. McMurry;M. P. Fleming
  19. J. Org. Chem. v.41 J. E. McMurry;L. R. Krepski

피인용 문헌

  1. Superbase‐Promoted Selective Cascade Cyclization Reaction of 1,5‐Diketones with Acetylenes to Methylene‐6,8‐dioxabicyclo[3.2.1]octanes vol.2013, pp.12, 1992, https://doi.org/10.1002/ejoc.201201700
  2. New reactions of alkynes with ketones in superbasic media vol.62, pp.11, 1992, https://doi.org/10.1007/s11172-013-0332-6
  3. Reactions of acetylenes in superbasic media. Recent advances vol.83, pp.7, 2014, https://doi.org/10.1070/rc2014v083n07abeh004425
  4. 1,5-Hydrogen Atom Transfer/Surzur-Tanner Rearrangement: A Radical Cascade Approach for the Synthesis of 1,6-Dioxaspiro[4.5]decane and 6,8-Dioxabicyclo[3.2.1]octane Scaffolds in Carbohydrate Systems vol.86, pp.21, 1992, https://doi.org/10.1021/acs.joc.1c01376