Financial supports from CNRS and ICSN are gratefully acknowledged. J.B.D. thanks ANR for a doctoral fellowship.
Cinchona Alkaloid Amide Catalyzed Enantioselective Formal [2+2] Cycloadditions of Allenoates and Imines: Synthesis of 2,4-Disubstituted Azetidines†
Article first published online: 28 APR 2011
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 50, Issue 23, pages 5356–5360, May 27, 2011
How to Cite
Denis, J.-B., Masson, G., Retailleau, P. and Zhu, J. (2011), Cinchona Alkaloid Amide Catalyzed Enantioselective Formal [2+2] Cycloadditions of Allenoates and Imines: Synthesis of 2,4-Disubstituted Azetidines. Angew. Chem. Int. Ed., 50: 5356–5360. doi: 10.1002/anie.201100706
- Issue published online: 23 MAY 2011
- Article first published online: 28 APR 2011
- Manuscript Received: 27 JAN 2011
- asymmetric synthesis;
- nitrogen heterocycles;
Mix and go: The quinidine amide 1 catalyzed [2+2] cycloaddition between N-sulfonylimines 2 and alkyl 2,3-butadienoates 3 afforded the R-configured azetidines 4 in excellent yields and enantioselectivities (M.S.=molecular sieve). The S enantiomer was obtained when a quinine amide catalyst, the pseudoenantiomer of 1, was used.