Asymmetric Synthesis of cis- and trans-2,5-Disubstituted Pyrrolidines from 3-Oxo Pyrrolidine 2-Phosphonates: Synthesis of (+)-Preussin and Analogs
Organic Letters2008Vol. 10(7), pp. 1433–1436
Citations Over TimeTop 10% of 2008 papers
Abstract
Pyrrolidine enones, derived from 3-oxo pyrrolidine 2-phosphonates and a HWE reaction with aldehydes, on Luche reduction give pyrrolidine allylic alcohols. The alcohols on hydrogenation (Pd/H2) give cis-2,5-disubstituted pyrrolidines and on treatment with TFA-NaBH3CN undergo a hydroxy directed reduction to trans-2,5-disubstituted pyrrolidines.
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