Evidence of asymmetric autocatalysis in organocatalytic reactions

Abstract

(Chemical Equation Presented) When product and catalyst are the same: The chiral product 3 of an asymmetric Mannich reaction (see scheme), investigated under various experimental conditions and by calculations, is shown to act as a chiral catalyst for its own formation (autocatalysis). A generally applicable catalytic cycle is proposed to involve equilibria between hydrogen-bonded substrate-product complexes. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.