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Rh(II)-Catalyzed Enantioselective Cyclopropanation of Olefins with Dimethyl Malonate via in Situ Generated Phenyliodonium Ylide

Citation

Muller, P and Ghanem, A, Rh(II)-Catalyzed Enantioselective Cyclopropanation of Olefins with Dimethyl Malonate via in Situ Generated Phenyliodonium Ylide, Organic Letters, 6, (23) pp. 4347-4350. ISSN 1523-7060 (2004) [Refereed Article]


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Copyright Statement

Copyright 2004 American Chemical Society

Official URL: http://pubs.acs.org

DOI: doi:10.1021/ol048159u

Abstract

Olefins are cyclopropanated with dimethyl malonate (1a) iodosylbenzene (PhIO) and a Rh(II) carboxylate catalyst via an in situ generated phenyliodonium ylide (1c). Enantioselectivities of up to 90% for 4-bromostyrene and 98% for pent-1-ene have been observed with (S)-N-4-bromo-1,8-naphthanoyl-tert-leucine (4c) as the chiral ligand. The same catalyst was effective for olefin cyclopropanation with Meldrum's acid, giving cyclopropanes with 96% (with styrene) and 87% ee (with pent-1-ene), respectively.

Item Details

Item Type:Refereed Article
Research Division:Chemical Sciences
Research Group:Organic Chemistry
Research Field:Organic Chemical Synthesis
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:Ghanem, A (Dr Ashraf Ghanem)
ID Code:58305
Year Published:2004
Web of Science® Times Cited:52
Deposited By:Austn Centre for Research in Separation Science
Deposited On:2009-09-25
Last Modified:2009-09-25
Downloads:0

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