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In Situ Enamine Activation in Aqueous Salt Solutions: Highly Efficient Asymmetric Organocatalytic Diels–Alder Reaction of Cyclohexenones with Nitroolefins

Authors

  • Dan-Qian Xu,

    1. State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou (China), Fax: (+86) 571-8832-0066
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  • Ai-Bao Xia,

    1. State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou (China), Fax: (+86) 571-8832-0066
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  • Shu-Ping Luo,

    1. State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou (China), Fax: (+86) 571-8832-0066
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  • Jie Tang,

    1. State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou (China), Fax: (+86) 571-8832-0066
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  • Shuai Zhang,

    1. State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou (China), Fax: (+86) 571-8832-0066
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  • Jun-Rong Jiang,

    1. State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou (China), Fax: (+86) 571-8832-0066
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  • Zhen-Yuan Xu

    1. State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou (China), Fax: (+86) 571-8832-0066
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  • This work was supported by the National Natural Science Foundation of China (No. 20772110) and the Program for Changjiang Scholars and Innovative Research Team in University of China.

Abstract

Deep-sea Diels–Alder: The asymmetric organocatalytic Diels–Alder reaction of cyclohexenones with aromatic nitroolefins can be carried out in seawater and brine. The reaction proceeds by an in situ enamine activation involving a one-step concerted addition pathway (see scheme).

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