Direct organocatalytic asymmetric approach to baylis-hillman-type products through a push-pull dienamine platform

Abstract

A general process for the asymmetric synthesis of highly substituted 3-alkyl-Hagemann's esters was achieved for the first time through organocatalytic Michael or Baylis-Hillman-type (BH-type) reaction of Hagemann's esters with β-nitrostyrenes in the presence of a catalytic amount of L-(3,5-Me2)2DPP/thiourea. We have discovered, for the first time, the chiral BH-type products from Hagemann's esters with β-nitrostyrenes by utilizing the push-pull dienamine platform. A general process for the asymmetric synthesis of 3-alkyl-Hagemann's esters was achieved for the first time through organocatalytic Baylis-Hillman-type (BH-type) reaction of Hagemann's esters with β-nitrostyrenes in the presence of a catalyticamount of L-(3,5-Me2)2DPP/thiourea. The chiral BH-type products were discovered by utilizing the push-pull dienamine platform. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.