Asymmetric Michael addition of amines to a,b-unsaturated esters are very promising because they afford units of b-amino acids that are a part of a number of naturally occurring bioactive compounds. So we investigated the asymmetric Michael addition of a chiral amino ether 2 to a variety of a,b-unsaturated esters and tandem Michael-aldol reaction, in which the enolate intermediate allowed to react with aldehyde for aimed to construction of three contiguous stereogenic centers. In addition, the chiral auxiliary linked to the amino group in the products was facilely removed and the products were converted to b-aminoesters and aldehydes 4 by reaction using N-iodosucinimide. Moreover, this aldehyde can be reclaimed to the chiral amine 2 by reductive amination with benzylamine.
