Asymmetric, catalytic, vinylogous aldol reactions using pyrrole-based dienoxy silanes. Enantioselective synthesis of alfa, beta -unsaturated gamma-butyrolactam synthons

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