Asymmetric routes towards polyfunctionalized pyrrolidines: Synthesis and reactivity of a chiral silyloxypyrrole

Article abstract of DOI:10.1016/0040-4039(95)02388-7

Starting from O-protected (R)-(-)-phenylglycinol, chiral silyloxypyrrole 5 was prepared in two steps and its reaction with achiral aldehydes under Mukaiyama's reaction conditions was investigated. Addition occurred at the C-5 position of the pyrrolidine ring with complete lk selectivity (except in the case of acetaldehyde) and a moderate to good diastereofacial (RR vs SS) selectivity.