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Wiley, Angewandte Chemie International Edition, 3(55), p. 1025-1029, 2015

DOI: 10.1002/anie.201509824

Wiley, Angewandte Chemie, 3(128), p. 1037-1041, 2015

DOI: 10.1002/ange.201509824

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[3,3]-Sigmatropic Rearrangement/Allylboration/Cyclization Sequence: Enantioenriched Seven-Membered-Ring Carbamates and Ring Contraction to Pyrrolidines

Journal article published in 2015 by Aurélie Macé ORCID, Sabrina Touchet, Patricia Andres, Fernando Cossío, Vincent Dorcet, François Carreaux, Bertrand Carboni
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

The combination of in situ generated α-isocyanato allylboronic esters and aldehydes afforded seven-membered-ring enecarbamates with high levels of diastereo- and enantiocontrol. They were easily converted into diversely substituted 1,3-oxazepan-2-ones. An unprecedented rearrangement of 5-acetoxy-7-aryl or styryl derivatives led to tetrasubstituted pyrrolidines. A computational study provides evidence on the feasibility of the proposed mechanism of this unusual ring contraction.