A New Chiral Primary Amine Catalyst: Application in Conjugate Additions

Significance

Maruoka and co-workers report the successful utilization of a novel bifunctional ­organocatalyst 1 in the asymmetric conjugate ­addition of α-heterosubstituted aldehydes to vinyl sulfones (for other reports on this reaction, see: A. Quintard, A. Alexakis Chem. Commun. 2010, 46, 4085; and references therein). The primary amine catalyst 1, synthesized in only a few steps from anthracene and fumaryl chloride, delivered the Michael adducts in generally high yields and enantioselectivities. 2,6-Dihydroxy benzoic acid turned out to be a crucial additive to increase the catalytic activity and ensure high enantiopurities.