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Issue 18, 2018
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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

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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 the one-time simultaneous construction of five continuous carbon-stereogenic centers for the straightforward and atom-economical 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 dr) and excellent enantioselectivities (up to >99% ee). In addition, it is probable that the weak coordination of an amide moiety on 1,1-disubstituted cyclopropenes with the copper complex is the main reason for the tuning of the stereoselectivity of the cycloaddition reaction.

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

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Publication details

The article was received on 25 Jul 2018, accepted on 31 Jul 2018 and first published on 01 Aug 2018


Article type: Research Article
DOI: 10.1039/C8QO00761F
Citation: Org. Chem. Front., 2018,5, 2759-2764
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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

    Y. Yuan, Z. Zheng, F. Ye, J. Ma, Z. Xu, X. Bai, L. Li and L. Xu, Org. Chem. Front., 2018, 5, 2759
    DOI: 10.1039/C8QO00761F

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