Enantioselective Amine Conjugate Addition

Significance

The paper in hand describes the first enantioselective organocatalytic amine conjugate 1,4-addition of N-silyloxycarbamate nucleophiles to α,β-unsaturated aldehydes. By forming an iminium ion, the unsaturated aldehydes are activated, using an imidazolidinone-type catalyst. The chemo- and stereoselective transformation leads to β-amino aldehydes in good yields and good to very good enantioselectivities. Furthermore, the authors have shown the synthesis of β-amino acids and 1,3-amino alcohols starting from enantioenriched β-amino aldehydes.