By Wyatt P., Warren S.
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S. Masamune, S. K. Ali, D. L. Snitman, and D. S. Garvey, Angew. , Int. , 1980, 19, 557 (see the footnote on page 558). 3. J. E. Dubois and M. , 1967, 4215; J. Chem. , Chem. , 1968, 1567; Bull Soc. Chim. , 1969, 3120 and 3553; P. Fellman and J. E. Dubois, Tetrahedron , 1978, 34, 1349. 4. C. H. Heathcock, J. Org. , 1980, 45, 1066. 5. H. E. Zimmerman and M. D. Traxler, J. Am. Chem.
LDA O 18; R = H, Me, OMe 2. RCHO R O (±)-anti-19 The ester prefers the conformation 20 because of the anomeric effect, the bonding interaction between one of the lone pairs on the ester oxygen atom and the antibonding orbital of the sigma bond of the carbonyl group, and normal conjugation with the other lone pair of electrons on the ester oxygen atom keeps the aryl group in the plane of the carbonyl group. Perhaps this means that the deprotonation by LDA 21 can take place only when the methyl group is anti to the C=O bond.
1968, 1567; Bull Soc. Chim. , 1969, 3120 and 3553; P. Fellman and J. E. Dubois, Tetrahedron , 1978, 34, 1349. 4. C. H. Heathcock, J. Org. , 1980, 45, 1066. 5. H. E. Zimmerman and M. D. Traxler, J. Am. Chem.