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Issue 7, 2013
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Rhodium-catalyzed enantioselective cyclopropanation of electron-deficient alkenes

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Abstract

The rhodium-catalyzed reaction of electron-deficient alkenes with substituted aryldiazoacetates and vinyldiazoacetates results in highly stereoselective cyclopropanations. With adamantylglycine derived catalyst Rh2(S-TCPTAD)4, high asymmetric induction (up to 98% ee) can be obtained with a range of substrates. Computational studies suggest that the reaction is facilitated by weak interaction between the carbenoid and the substrate carbonyl but subsequently proceeds via different pathways depending on the nature of the carbonyl. Acrylates and acrylamides result in the formation of cyclopropanation products while the use of unsaturated aldehydes and ketones results in the formation of epoxides.

Graphical abstract: Rhodium-catalyzed enantioselective cyclopropanation of electron-deficient alkenes

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Publication details

The article was received on 13 Feb 2013, accepted on 12 Apr 2013 and first published on 15 Apr 2013


Article type: Edge Article
DOI: 10.1039/C3SC50425E
Chem. Sci., 2013,4, 2844-2850

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    Rhodium-catalyzed enantioselective cyclopropanation of electron-deficient alkenes

    H. Wang, D. M. Guptill, A. Varela-Alvarez, D. G. Musaev and H. M. L. Davies, Chem. Sci., 2013, 4, 2844
    DOI: 10.1039/C3SC50425E

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