DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF 1,2-AMINO ALCOHOLS FROM GLYCOL ALDEHYDE HYDRAZONES - ASYMMETRIC-SYNTHESIS OF (R,R)-STATIN

Electrophilic α‐alkylation and nucleophilic 1,2‐addition to glycol aldehyde 1 (P = protecting group) affords syn‐1,2‐amino alcohols 2 in good yields and with high selectivities (89 to <99% de, 94 to ≥99% ee). This method, in which 1 is first converted into a chiral hydrazone, provides a flexible, direct route to γ‐amino‐β‐hydroxycarboxylic acids such as statin 3, an essential component in natural peptidic enzyme inhibitors (R1 = CH2 = CHCH2, R2 = iBu). (Figure Presented.) Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany