Highly Regio-, Diastereo-, and Enantioselective 1,6-and 1,8-Additions of Azlactones to Di- and Trienyl N-Acylpyrroles

A vinylog of Michael addition (1,6-addition) of azlactones to delta-substituted dienyl N-acylpyrroles been developed with virtually complete 1,6-diastereo-, and enantioselectivities by means of chiral P-spiro triaminoiminophosphorane as a catalyst. This system has been successfully extended to an unprecedented bis-vinylog of Michael addition (1,8 addition) of azlactones to zeta-substituted trienyl N-acylpyrroles with high levels of regio- and stereocontrol.