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)
see article for more reactions
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.
see article for more examples