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[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
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01240655
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Submitted on : Wednesday, December 9, 2015 - 1:37:51 PM
Last modification on : Friday, July 10, 2020 - 4:24:59 PM

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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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