Remote Asymmetric Induction. Stereo- and Enantioselective Synthesis of Symmetrical and Unsymmetrical 1,4-Diols

Article abstract of DOI:10.1016/S0957-4166(00)80267-0

Nucleophilic addition of Grignard reagents to the tricyclic lactols 4 or 5 provides with very high selectivity syn or anti 1,4-diols, so that, starting from the scalemic lactol 1a, three of the four possible diastereoisomeric 1,4-diols 7 or 9 can be obtained.This new example of remote asymmetric induction is illustrated by the synthesis of optically pure (2R,5R)-2,5-hexanediol and (3S,6R)-4-decen-3,6-diol.