Organic letters

Preparation of chiral 3-arylpyrrolidines via the enantioselective 1, 4-addition of arylboronic acids to fumaric esters catalyzed by Rh (I)/chiral diene complexes

YC Chung, D Janmanchi, HL Wu

Index: Chung, Yu-Chiang; Janmanchi, Damodar; Wu, Hsyueh-Liang Organic Letters, 2012 ,  vol. 14,  # 11  p. 2766 - 2769

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Citation Number: 24

Abstract

A highly efficient rhodium-catalyzed protocol for the preparation of 2-arylsuccinic esters and 3-arylpyrrolidines of high optical purity has been achieved. In the presence of 1 mol% of a chiral diene/Rh (I) catalyst, asymmetric addition of various arylboronic acids to di-tert-butyl fumarate (3c) provides the corresponding adducts in up to 99% yield and 94→ 99.5% ee. Excellent enantioselectivities were also observed in the regio-and enantioselective ...