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Issue 99, 2013
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Highly enantioselective synthesis of chiral 7-ring O- and N-heterocycles by a one-pot nitro-Michael–cyclization tandem reaction

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Abstract

A concise enantioselective approach to synthesise medium-sized 7-ring O- and N-heterocycles has been developed. The synthetic strategy relies on an organocatalytic nitro-Michael–nitrile oxide cycloaddition tandem reaction, leading to the corresponding chiral benzoxe- and benzazepine derivatives containing an additional fused dihydroisoxazoline ring in good yields and excellent enantioselectivities (up to 97% ee).

Graphical abstract: Highly enantioselective synthesis of chiral 7-ring O- and N-heterocycles by a one-pot nitro-Michael–cyclization tandem reaction

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Publication details

The article was received on 27 Sep 2013, accepted on 17 Oct 2013 and first published on 21 Oct 2013


Article type: Communication
DOI: 10.1039/C3CC47397J
Chem. Commun., 2013,49, 11665-11667

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    Highly enantioselective synthesis of chiral 7-ring O- and N-heterocycles by a one-pot nitro-Michael–cyclization tandem reaction

    R. Rohlmann, C. Daniliuc and O. G. Mancheño, Chem. Commun., 2013, 49, 11665
    DOI: 10.1039/C3CC47397J

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