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Issue 10, 2011
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Catalytic asymmetric [4 + 2] additions with aliphatic nitroalkenes

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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

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Publication details

The article was received on 26 May 2011, accepted on 22 Jun 2011 and first published on 18 Jul 2011


Article type: Edge Article
DOI: 10.1039/C1SC00326G
Chem. Sci., 2011,2, 1940-1944

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    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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