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Issue 17, 2014
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Catalytic asymmetric [3+2] cycloaddition of aromatic aldehydes with oxiranes by C–C bond cleavage of epoxides: highly efficient synthesis of chiral 1,3-dioxolanes

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Abstract

A novel and efficient N,N′-dioxide–Gd(III) complex was developed for the highly diastereo- and enantioselective [3+2] cycloaddition of aryl oxiranyl diketones and aldehydes via C–C bond cleavage of oxiranes. The corresponding chiral 1,3-dioxolanes were obtained in excellent yields (up to 99%) with high diastereoselectivities (>95 : 5 dr) and enantioselectivities (up to 91% ee). Moreover, a possible transition model was proposed to explain the origin of the asymmetric induction.

Graphical abstract: Catalytic asymmetric [3+2] cycloaddition of aromatic aldehydes with oxiranes by C–C bond cleavage of epoxides: highly efficient synthesis of chiral 1,3-dioxolanes

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Publication details

The article was received on 11 Nov 2013, accepted on 26 Dec 2013 and first published on 15 Jan 2014


Article type: Communication
DOI: 10.1039/C3CC48606K
Chem. Commun., 2014,50, 2161-2163

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    Catalytic asymmetric [3+2] cycloaddition of aromatic aldehydes with oxiranes by C–C bond cleavage of epoxides: highly efficient synthesis of chiral 1,3-dioxolanes

    W. Chen, L. Lin, Y. Cai, Y. Xia, W. Cao, X. Liu and X. Feng, Chem. Commun., 2014, 50, 2161
    DOI: 10.1039/C3CC48606K

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