Asymmetric, catalytic, vinylogous aldol reactions using pyrrole-based dienoxy silanes. Enantioselective synthesis of α,β-unsaturated γ-butyrolactam synthons

摘要

A practical, catalytic and enantioselective vinylogous Mukaiyama aldol reaction between 2-silyloxypyr-role donors and aromatic or heteroaromatic aldehyde acceptors is described. Using an enantiopure bisphosphoramide catalyst in conjunction with SiCl4, a variety of α,β-unsaturated-8-hydroxylated Y-butyrolactam compounds were synthesized in high yields and with good to excellent levels of site-, diastereo-and enantioselectivity.