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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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Article information


Submitted
27 Sep 2013
Accepted
17 Oct 2013
First published
21 Oct 2013

Chem. Commun., 2013,49, 11665-11667
Article type
Communication

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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