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Highly efficient desymmetrization of cyclopropenes to azabicyclo[3.1.0]hexanes with five continuous stereogenic centers by copper-catalyzed [3+2] cycloadditions

Abstract

An unprecedented copper-catalyzed desymmetrization/cycloaddition of 1,1-disubstituted cyclopropenes to azabicyclo[3.1.0]hexane-based heterocycles containing cyclopropane and pyrrolidine motif has been developed. The salient features of one-time simultaneous construction of five continuous carbon-stereogenic centers for the straightforward and atom-economic synthesis of chiral azabicyclo[3.1.0]hexane derivatives include a general and broad substrate scope with high yields as well as excellent diastereoselectivities (>99:1 d.r.) and excellent enantioselectivities (up to >99% ee). In addition, it is probably that the weak coordination of amide moiety on 1,1-disubstituted cyclopropenes with the copper complex is the main reason for the tuning the stereoselectivity of the cycloaddition reaction.

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Publication details

The article was accepted on 31 Jul 2018 and first published on 01 Aug 2018


Article type: Review Article
DOI: 10.1039/C8QO00761F
Citation: Org. Chem. Front., 2018, Accepted Manuscript
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    Highly efficient desymmetrization of cyclopropenes to azabicyclo[3.1.0]hexanes with five continuous stereogenic centers by copper-catalyzed [3+2] cycloadditions

    L. Xu, Y. Yuan, Z. Zheng, F. Ye, J. Ma, Z. Xu, X. Bai and L. Li, Org. Chem. Front., 2018, Accepted Manuscript , DOI: 10.1039/C8QO00761F

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