Facile synthesis of optically active 2-hydroxymethyl-4-methylenecyclohexanol. De novo synthesis of dideoxycarbocyclic sugars

Tetrahedron Letters

Volumn 37, Issue 1, 1996, Pages 3-6

  Jung, Michael E ^a   Cho, Young M ^a   Jung, Young H ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANOL DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030025329     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02067-5     Document Type: Article

References (31)

1. Presented at the 33rd GECO Conference, Corsica, France, September 1992.
2. American Chemical Society Arthur C. Cope Scholar, 1995.
3. For excellent reviews, see: a) Nishizawa, M.; Noyori, R. "Reduction of C=X to CHXH by Chirally Modified Hydride Reagents," Chapter 1.7 in Comprehensive Organic Synthesis, Trost, B. M., Ed.; Pergamon; Oxford, 1991; Vol. 8, pp. 159-182.
4. b) Jones, B. J. "Reduction of C=X to CHXH Using Enzymes and Microorganisms," Chapter 1.8 in Comprehensive Organic Synthesis, Trost, B. M., Ed.; Pergamon; Oxford, 1991; Vol. 8, pp. 183-210 and references in both of the above.
5. a) For a review of enantioselective cyclopropanation see: Helquist, P. "Methylene and Nonfunctionalized Alkylidene Transfer to Form Cyclopropanes," Chapter 4.6 in Comprehensive Organic Synthesis, Trost, B. M., Ed.; Pergamon; Oxford, 1991; Vol. 4, pp. 951-997.
6. b) For a review of Diels-Alder reactions, see: Oppolzer, W. "Intermolecular Diels-Alder Reactions," Chapter 4.1 in Comprehensive Organic Synthesis, Trost, B. M., Ed.; Pergamon; Oxford, 1991; Vol. 5, pp. 315-399.
7. For a review of enantioselective alkylations, see: Caine, D. "Alkylations of Enols and Enolates," Chapter 1.1 in Comprehensive Organic Synthesis, Trost, B. M., Ed.; Pergamon; Oxford, 1991; Vol. 3, pp. 1-63.
8. For a review of ester enolate Claisen rearrangements, see: Altenbach, H.-J. "Functional Group Transformations via Allyl Rearrangement," Chapter 4.5 in Comprehensive Organic Synthesis, Trost, B. M., Ed.; Pergamon; Oxford, 1991; Vol. 6, pp. 829-871.
9. a) Finn, M. G.; Sharpless, K. B. in Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1985; Vol. 5, Ch. 8, pp 247-308.
10. b) Hanson, R. M.; Sharpless, K. B. J. Org. Chem. 1986, 51, 1922.
11. c) Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237.
12. d) Rossiter, B. E.; Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 464.
13. e) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974.
14. a) Johnson, M. R.; Nakata, T.; Kishi, Y. Tetrahedron Lett. 1979, 4343.
15. b) Behrens, C. H.; Sharpless, K. B. Aldrichim. Acta 1983, 16, 67.
16. Trost, B. M.; Chan, D. M. T.; Nanninga, T. N. Org. Synth. 1984, 62, 58; Organic Syntheses; Wiley: New York, 1990; Collect. Vol. VII, p. 266.
17. Trost, B. M.; Chan, D. M. T.; Nanninga, T. N. Org. Synth. 1984, 62, 58; Organic Syntheses; Wiley: New York, 1990; Collect. Vol. VII, p. 266.
18. Trost, B. M.; Chan, D. M. T.; Nanninga, T. N. Org. Synth. 1984, 62, 58; Organic Syntheses; Wiley: New York, 1990; Collect. Vol. VII, p. 266.
19. Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637.
20. For examples of the use of this reagent for epoxide openings, see: a) Jung, M. E.; Gardiner, J. M. J. Org. Chem. 1991, 56, 2614;
21. b) Maruoka, K.; Sano, H.; Yamamoto, H. Chem. Lett. 1985, 599.
22. Nohira, H.; Ehara, K.; Miyashita, A. Bull. Chem. Soc. Jpn. 1970, 43, 2230.
23. Sharpless, K. B.; Caron, M. J. Org. Chem. 1985, 50, 1557. For a cyclic example where attack at C3 is again favored over attack at C2, see: Morgans, D. J., Jr.; Sharpless, K. B.; Traynor, S. G. J. Am. Chem. Soc. 1981, 103, 462.
24. Sharpless, K. B.; Caron, M. J. Org. Chem. 1985, 50, 1557. For a cyclic example where attack at C3 is again favored over attack at C2, see: Morgans, D. J., Jr.; Sharpless, K. B.; Traynor, S. G. J. Am. Chem. Soc. 1981, 103, 462.
25. a) Molander, G. A.; Andrews, S. W. J. Org. Chem. 1989, 54, 3114.
26. b) Proctor, G.; Russell, A. T.; Murphy, P. J.; Tan, T. S.; Mather, A. N. Tetrahedron 1988, 44, 3953.
27. c) Petterson, L.; Frejd, T.; Magnusson, G. Tetrahedron Lett. 1987, 28, 2753.
28. 14b reports the formation of products of both C2 and C3 attack but couldn't isolate them, prove the structures, or determine a yield.
29. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734.
30. For examples of 5-endo-trig cyclizations of allylsilanes on aldehydes, see: a) Lee, T. V.; Roden, F. S. Tetrahedron Lett. 1990, 31, 2067.
31. b) Sarkar, T. K.; Andersen, N. H. Tetrahedron Lett. 1978, 3513.