Issue 10, 2011

Catalytic asymmetric [4 + 2] additions with aliphatic nitroalkenes

Abstract

We describe an unprecedented cycloaddition reaction of 2-pyrones with aliphatic nitroalkenes catalyzed by a new bifunctional cinchona alkaloid-derived catalyst bearing a bulky TIPS-ether at the 9-position. The [2.2.2] bicyclic adducts were obtained in good yield with excellent diastereo- and enantioselectivity. Carbon isotope effects were measured by 13C NMR and are indicative of a stepwise mechanism. Finally, a synthetic application is demonstrated, highlighting the utility of the cycloadducts.

Graphical abstract: Catalytic asymmetric [4 + 2] additions with aliphatic nitroalkenes

Supplementary files

Article information

Article type
Edge Article
Submitted
26 May 2011
Accepted
22 Jun 2011
First published
18 Jul 2011

Chem. Sci., 2011,2, 1940-1944

Catalytic asymmetric [4 + 2] additions with aliphatic nitroalkenes

K. J. Bartelson, R. P. Singh, B. M. Foxman and L. Deng, Chem. Sci., 2011, 2, 1940 DOI: 10.1039/C1SC00326G

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