We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
[3,3]-Sigmatropic Rearrangement/Allylboration/Cyclization Sequence: Enantioenriched Seven-Membered-Ring Carbamates and Ring Contraction to Pyrrolidines.
- Authors
Macé, Aurélie; Touchet, Sabrina; Andres, Patricia; Cossío, Fernando; Dorcet, Vincent; Carreaux, François; Carboni, Bertrand
- 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.
- Subjects
PYRROLIDINE; ALLYLBORATION; ORGANIC synthesis; RING formation (Chemistry); CHEMICAL reactions
- Publication
Angewandte Chemie International Edition, 2016, Vol 55, Issue 3, p1025
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201509824