[3,3]-Sigmatropic Rearrangement/Allylboration/Cyclization Sequence: Enantioenriched Seven-Membered-Ring Carbamates and Ring Contraction to Pyrrolidines - Université de Rennes Access content directly
Journal Articles Angewandte Chemie Year : 2016

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

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

Dates and versions

hal-01240655 , version 1 (09-12-2015)

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Aurélie Macé, Sabrina Touchet, Patricia Andres, Fernando Cossío, Vincent Dorcet, et al.. [3,3]-Sigmatropic Rearrangement/Allylboration/Cyclization Sequence: Enantioenriched Seven-Membered-Ring Carbamates and Ring Contraction to Pyrrolidines. Angewandte Chemie, 2016, 55 (3), pp.1025-1029 ⟨10.1002/anie.201509824⟩. ⟨hal-01240655⟩
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