Rhodium-catalyzed enantioselective cyclopropanation of electron-deficient alkenes

Hengbin Wang, David M. Guptill, Adrian Varela-Alvarez, Djamaladdin G. Musaev, Huw M.L. Davies

Research output: Contribution to journalArticlepeer-review

76 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)2844-2850
Number of pages7
JournalChemical Science
Volume4
Issue number7
DOIs
StatePublished - Jun 4 2013

Fingerprint

Dive into the research topics of 'Rhodium-catalyzed enantioselective cyclopropanation of electron-deficient alkenes'. Together they form a unique fingerprint.

Cite this