A General Asymmetric Formal Synthesis of Aza-Baylis-Hillman Type Products under Bifunctional Catalysis

Abstract

A new organocatalytic strategy for the synthesis of enantioenriched aza-Baylis-Hillman type products via a frustrated vinylogous reaction is presented. This process proceeds under mild conditions with good yields, completed Z/E selectivity and excellent enantioselectivities. Moreover, easy derivatizations of the final products led to important building blocks of organic synthesis such as 1,3-aminoalcohols and Lewis base catalysts.

Keywords: Baylis-Hillman reaction; asymmetric synthesis; bifunctional catalysis; silyl-enol ethers; thiourea.