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Issue 74, 2018
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Asymmetric synthesis of polysubstituted methylenecyclobutanes via catalytic [2+2] cycloaddition reactions of N-allenamides

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Abstract

A highly enantioselective [2+2] cycloaddition reaction of alkylidene malonates with the internal C[double bond, length as m-dash]C bond of N-allenamides was developed with a MgII/N,N′-dioxide complex as a catalyst. Various polysubstituted methylenecyclobutanes were afforded in good yields (up to 99%) and excellent enantioselectivities (up to 96% ee) under mild conditions. The utility of the donor–acceptor cyclobutane product was demonstrated as a masked 1,4-dipole in the formal [4+2] annulation reaction with a silyl enol ether.

Graphical abstract: Asymmetric synthesis of polysubstituted methylenecyclobutanes via catalytic [2+2] cycloaddition reactions of N-allenamides

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Publication details

The article was received on 07 Aug 2018, accepted on 23 Aug 2018 and first published on 23 Aug 2018


Article type: Communication
DOI: 10.1039/C8CC06416D
Citation: Chem. Commun., 2018,54, 10511-10514

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    Asymmetric synthesis of polysubstituted methylenecyclobutanes via catalytic [2+2] cycloaddition reactions of N-allenamides

    X. Zhong, Q. Tang, P. Zhou, Z. Zhong, S. Dong, X. Liu and X. Feng, Chem. Commun., 2018, 54, 10511
    DOI: 10.1039/C8CC06416D

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