Support to M.P.D. from the National Institutes of Health (GM 46503) is gratefully acknowledged. W.H. thanks MOST of China (2011CB808600) and the NSFC (21125209, 20932003) for sponsorship.
Rhodium(II)- and Copper(II)-Catalyzed Reactions of Enol Diazoacetates with Nitrones: Metal Carbene versus Lewis Acid Directed Pathways†
Article first published online: 4 MAY 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 24, pages 5900–5903, June 11, 2012
How to Cite
Qian, Y., Xu, X., Wang, X., Zavalij, P. J., Hu, W. and Doyle, M. P. (2012), Rhodium(II)- and Copper(II)-Catalyzed Reactions of Enol Diazoacetates with Nitrones: Metal Carbene versus Lewis Acid Directed Pathways. Angew. Chem. Int. Ed., 51: 5900–5903. doi: 10.1002/anie.201202525
- Issue published online: 5 JUN 2012
- Article first published online: 4 MAY 2012
- Manuscript Received: 31 MAR 2012
- National Institutes of Health. Grant Number: GM 46503
- MOST of China. Grant Number: 2011CB808600
- NSFC. Grant Numbers: 21125209, 20932003
- homogeneous catalysis;
A complimentary cat.: Copper(II) hexafluoroantimonate catalyzes the formal [3+3] cycloaddition of Lewis acid activated nitrones and vinyl diazoacetates to produce 3,6-dihydro-1,2-oxazines in yields of up to 96 % and diastereoselectivities greater than 25:1 (see scheme). This process compliments the metal carbene pathway that is catalyzed by rhodium(II) species.