Synthesis of highly functionalized 2,5-disubstituted pyrrolidines via an aza-MoritaeBayliseHillman-type reaction

Abstract

This paper is dedicated with admiration to Professor Steven Ley on the award of the Tetrahedron Prize for creativity in organic chemistry. Many congratulations! a b s t r a c t An aza-MoritaeBayliseHillman-type reaction of Michael acceptors with 5-substituted cyclic N,O-acetals derived from pyrrolidines has been investigated. It has been found that the combination of Me 2 S and TMSOTf work well with unhindered and reactive enals and enones whilst the use of quinuclidine and TMSOTf is superior for more hindered Michael acceptors. The reactions lead to 2,5-trans-disubstituted pyrrolidines with good to excellent diastereoselectivity. The origin of the selectivity is discussed