Use of a new spirophosphine to achieve catalytic enantioselective [4 + 1] annulations of amines with allenes to generate dihydropyrroles

Journal of the American Chemical Society
Søren Kramer, Gregory C Fu

Abstract

Due in part to the common occurrence of five-membered nitrogen heterocycles in bioactive molecules, the discovery of methods for the enantioselective synthesis of such structures is a useful endeavor. Building on a single example by Tong of a phosphine-catalyzed [4 + 1] annulation of an amine with an allene that furnished an achiral dihydropyrrole in 22% yield, we have developed, with the aid of a new chiral spirophosphine catalyst, a method with increased utility, specifically, improved yield, enhanced scope (the use of γ-substituted allenes), and good ee. The enantioenriched dihydropyrrole products can be transformed into other interesting families of compounds with very good stereoselectivity.

References

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Citations

Feb 26, 2016·Science·Quirin M KainzGregory C Fu
Feb 4, 2016·Organic Letters·Xiaohong ChenJustin T Mohr
Jul 8, 2015·Journal of the American Chemical Society·Peng-Fei ZhengYing-Chun Chen
Jun 17, 2016·Journal of the American Chemical Society·Chunjie Ni, Xiaofeng Tong
Mar 19, 2016·Chemistry : a European Journal·Min ShiFeng-Chen Shi
Jul 20, 2016·Angewandte Chemie·Lina MaZhiping Li
Aug 7, 2019·Chemical Communications : Chem Comm·Zhenjie GanZheng Duan
Nov 23, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yangyan LiXiao Shen
Oct 24, 2019·Organic & Biomolecular Chemistry·Julie E LaudenschlagerMichael K Hilinski
Dec 16, 2020·Chemical Communications : Chem Comm·Yifan HuangHongchao Guo
Mar 11, 2021·Chemical Communications : Chem Comm·Yueqi ZhangXiaofeng Tong
Feb 20, 2019·The Journal of Organic Chemistry·Cong-Shuai WangFeng Shi

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