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Chemo- and Diastereoselective Synthesis of Pyrrolidines from Aroylformates and δ-Tosylamino Enones via P(NMe2)3-Mediated Reductive Amination/Base-Catalyzed Michael Addition Cascade

Rongfang Liu, Jialin Liu, Jilei Cao, Ruifeng Li, Rong Zhou*, Yan Qiao and Wen-Chao Gao*

*College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024, P.R. China Email: zhourongtyut.edu.cn, gaowenchaotyut.edu.cn

R. Liu, J. Liu, J. Cao, R. Li, R. Zhou, Y. Qiao, W.-C. Gao, Org. Lett., 2020, 22, 6922-6926.

DOI: 10.1021/acs.orglett.0c02453 (free Supporting Information)


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Abstract

A P(NMe2)3-mediated tandem (1 + 4) annulation between aroylformates and δ-tosylamino enones provides functionalized pyrrolidines in good yields with exclusive chemoselectivity and high diastereoselectivity. The reaction proceeds through an unprecedented P(NMe2)3-mediated reductive amination/base-catalyzed Michael addition cascade.

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proposed mechanism



Key Words

pyrrolidines, tris(dimethylamino)phosphine


ID: J54-Y2020