Journal of the Chemical Society. Perkin transactions I p. 1220 - 1226 (1981)
Update date:2022-08-04
Topics:
Westhuizen, Jan H. van der
Ferreira, Daneel
Roux, David G.
Photolytic rearrangements of those 2,3-trans-3,4-trans- and 2,3-trans-3,4-cis-4-arylflavan-3-ols in which the nucleophilicity of D-ring (4-aryl group) functionality exceeds that of the A-ring, provide the first access to 2,3-cis-3,4-cis-diastereoisomers.The circular dichroism of these new isomers is at variance with the proposed general rule for assessing the absolute configuration at C-4.In terms of the aromatic quadrant rule such discrepancies correlate with deviations from the preferred C-ring conformations.
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Doi:10.1021/ja00395a044
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(1981)
