Issue 7, 2013

Rhodium-catalyzed enantioselective cyclopropanation of electron-deficient alkenes

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

Supplementary files

Article information

Article type
Edge Article
Submitted
13 Feb 2013
Accepted
12 Apr 2013
First published
15 Apr 2013

Chem. Sci., 2013,4, 2844-2850

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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