Highly enantioselective Ag(i)-catalyzed [3 + 2] cycloaddition of azomethine ylides.

James M Longmire, Bin Wang, Xumu Zhang

Index: J. Am. Chem. Soc. 124(45) , 13400-1, (2002)

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Abstract

A highly reactive Ag(I)-catalyzed [3 + 2] cycloaddition of azomethine ylides is founded using AgOAc as the catalytic precursor and phosphines as ligands. Using a new bis-ferrocenyl amide phosphine (FAP) as the ligand, we found that high enantioselectivities (up to 97% ee) have been achieved in the [3 + 2] cycloaddition of azomethine ylides. Up to four stereogenic centers can be established in this multicomponent coupling reaction from readily available materials such as aldehydes, aminoesters, and dipolarophiles.