Organic letters

Highly enantioselective synthesis of γ-nitro heteroaromatic ketones in a doubly stereocontrolled manner catalyzed by bifunctional thiourea catalysts based on …

X Jiang, Y Zhang, ASC Chan, R Wang

Index: Jiang, Xianxing; Zhang, Yifu; Chan, Albert S. C.; Wang, Rui Organic Letters, 2009 , vol. 11, # 1 p. 153 - 156

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Citation Number: 97

Abstract

A new class of dehydroabietic amine-substituted primary amine-thiourea bifunctional catalysts were designed and synthesized. The doubly stereocontrolled organocatalytic conjugate addition of a variety of heterocycles-bearing ketones to nitroalkenes was investigated for the first time, affording (S)-or (R)-γ-nitro heteroaromatic ketones with excellent enantioselectivities (up to ee> 99%). Furthermore, the nearly optically pure γ- ...