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Highly Enantioselective Synthesis of γ-Nitro Heteroaromatic Ketones in a Doubly Stereocontrolled Manner Catalyzed by Bifunctional Thiourea Catalysts Based on Dehydroabietic Amine: A Doubly Stereocontrolled Approach to Pyrrolidine Carboxylic Acids

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journal contribution
posted on 01.01.2009 by Xianxing Jiang, Yifu Zhang, Albert S. C. Chan, Rui Wang
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-nitro heteroaromatic ketones can be readily transformed into chiral pyrrolidine carboxylic acids.