Preference for 6-Exo-Trigonal closures of ω-hydroxy-αβ- unsaturated esters

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 3, 1977, Pages 77-

  Baldwin, Jack E ^a   Reiss, James A ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

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[No Author keywords available]

Indexed keywords

EID: 37049111994     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39770000077     Document Type: Article

References (15)

1. J. E. Baldwin, J.C.S. Chem. Comm., 1976, 734.
2. J. E. Baldwin, J. Cutting, W. Dupont, L. Kruse, L. Silberman, and R. C. Thomas, J.C.S. Chem. Comm., 1976, 736.
3. L. D. Bergelson, E. V. Dyatlovitskaya, and M. M. Shemyakin, Izvest. Akad. Nauk S.S.S.R. Otdel. khim. Nauk, 1963, 506.
4. L. D. Bergelson, E. V. Dyatlovitskaya, and M. M. Shemyakin, Chem. Abs., 1963, 59, 3766d.
5. G. I. Fray, R. H. Jaeger, E. D. Morgan, R. Robinson, and A. D. B. Sloan, Tetrahedron, 1961, 15, 18.
6. E. R. H. Jones, T. Y. Shen, and M. C. Whiting, J. Chem. Soc., 1950, 230.
7. A. D. Harmon and C. R. Hutchinson, J. Org. Chem., 1975, 40, 3474.
8. Smith, Kline and French Laboratories, B.P. 1, 099, 209 (Chem. Abs., 1968, 69, P10361g), 1, 3-Dienes and α β-unsaturated aldehydes and ketones are known to have a preferred s-trans conformation.
9. E. Eliel, ‘Stereochemistry of Carbon Compounds,’ McGraw-Hill, New York, 1962, p. 331.
10. The stereochemistry of α β-unsaturated esters is less clear and is solvent dependent but the s-trans conformation appears to be preferred: D. B. Cunliffe-Jones, Spectrochim. Acta, 1965, 21, 245.
11. R. J. W. LeFevre and K. M. S. Sundaram, J. Chem. Soc., 1963, 1880.
12. R. J. W. LeFevre and K. M. S. Sundaram, J. Chem. Soc., 1963, 3188.
13. R. E. Bowman and J. F. Cavalla, J. Chem. Soc., 1954, 1171.
14. For example see: H. B. Burgi, J. D. Dunitz, J.-M. Lehn, and G. Wipff, Tetrahedron, 1974, 30, 1563.
15. H. B. Burgi, J. D. Dunitz, and E. Shefter, J. Amer. Chem. Soc., 1973, 95, 5065.