Asymmetric Synthesis of Monoprotected Double Allylic Alcohols

Abstract

The enantioselective synthesis of mono-TBS protected, double allylic alcohols 5 (ee = 90-94%) employing the SAMP/RAMP-hydrazone methodology is reported. Acetonide protected, α-substituted ketodiols 2 were synthesized from SAMP-hydrazone 1 which were converted to exocyclic olefins 3 by a racemization-free Wittig reaction. Acidic acetal cleavage to 4 followed by selective TBS protection furnished title compounds 5 in very good overall yields and enantiomeric excesses.

asymmetric synthesis - hydrazones - Wittig reaction - allylic alcohols - protecting groups

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