Acyclic Stereoselection. 11. Double Stereodifferentiation as a Method for Achieving Superior Cram's Rule Selectivity in Aldol Condensations with Chiral Aldehydes

Journal of Organic Chemistry

Volumn 46, Issue 7, 1981, Pages 1296-1309

  Heathcock, Clayton H ^a   White, Charles T ^b   Morrison, James Jeffery ^b   VanDerveer, Don ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845556810     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00320a014     Document Type: Article

References (31)

1. C.T. White and C. H. Heathcock, J. Org. Chem., 46, 191 (1981).
2. C. H. Heathcock and C. T. White, J. Am. Chem. Soc., 101, 7076 (1979).
3. S. Hanessian, 179th National Meeting of the American Chemical Society, Houston, TX, Mar 25, 1980.
4. C. H. Heathcock, C. T. Buse, W. A. Kleschick, M. C. Pirrung, J. E. Sohn, and J. Lampe, J. Org. Chem., 45, 1066 (1980), and references therein.
5. M. Hirama and S. Masamune, Tetrahedron Lett., 2225 (1979)
6. M. Hirama, D. S. Garvey, L.D.-L. Lu, and S. Masamune, Tetrahedron Lett., 3937 (1979).
7. D. A. Evans, E. Vogel, and J. V. Nelson, J. Am. Chem. Soc., 101, 6120 (1979).
8. A. Horeau, H.-B. Kagan, and J.-P. Vigneron, Bull. Soc. Chim. Fr., 3795 (1968).
9. Y. Izumi and A. Tai, “Stereodifferentiating Reactions”, Kodanshar Ltd., Tokyo, Academic Press, New York, 1977.
10. W. Glen, G. Myers, and G. Grant, J. Chem. Soc., 2568 (1951).
11. E. J. Corey and J. W. Suggs, Tetrahedron Lett., 2647 (1975).
12. R. F. Brady, Jr., Carbohydr. Res., 15, 35 (1970).
13. D. Seebach and E. J. Corey, J. Org. Chem., 40, 231 (1975)
14. E. J. Corey and B. W. Erickson, J. Org. Chem., 36, 3553 (1971).
15. A. L. Raymond and E. F. Schroeder, J. Am. Chem. Soc., 70, 2785 (1948).
16. K. Freudenberg and R. M. Hixon, Ber. Dtsch. Chem. Ges., 2119 (1923).
17. M. A. Oldham and J. Honeyman, J. Chem. Soc., 987 (1946).
18. C. H. Heathcock, M. C. Pirrung, and J. E. Sohn, J. Org. Chem., 44, 4294 (1979).
19. H. O. House, D. S. Crumrine, A. Y. Teranishi, and H. D. Olmstead, J. Am. Chem. Soc., 95, 3310 (1973).
20. See C. Djerassi, “Optical Rotatory Dispersion; Applications to Organic Chemistry”, McGraw-Hill, New York, 1960.
21. M. Windholz, Ed., “The Merck Index”, 9th ed., Merck and Co., Rathway, NJ, 1977.
22. C. H. Heathcock, S. D. Young, J. P. Hagen, M. C. Pirrung, C. T. White, and D. VanDerveer, J. Org. Chem., 45, 3846 (1980).
23. E. Baer and H. O. L. Fischer, J. Biol. Chem., 128, 463 (1939).
24. S. B. Baker, J. Am. Chem. Soc., 74, 827 (1952).
25. D. Seebach, S. B. Schriftenreike des Fonds der Chemische Industrie, 1975.
26. D. Seebach, H.-O. Kalinowsky, B. Bastani, G. Cross, H. Daum, N. DuPreez, V. Ehrig, W. Langer, C. Nüssler, H.-A. Oei, and M. Schmidt, Helv. Chim. Acta, 60, 301 (1977).
27. J. Smejkal and L. Kaxoda, Collect. Czech. Chem. Commun., 38, 1981 (1973).
28. T. Matsumoto, I. Tanaka, and K. Fukui, Bull. Chem. Soc. Jpn., 44, 3378 (1971).
29. J. Canciell, J. Gabard, and J. Jacques, Bull. Soc. Chim. Fr., 231 (1968).
30. International Tables for X-Ray Crystallography”, Vol. I, Kynoch Press, Birmingham, England, 1952.
31. International Tables for X-Ray Crystallography”, Vol. IV, Kynoch Press, Birmingham, England, 1974, pp 99-101, 149-150.