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Synfacts 2019; 15(09): 1013
DOI: 10.1055/s-0039-1690581
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Simmons–Smith Cyclopropanation: The Charette Modification

Contributor(s):
Mark Lautens
,
Egor M. Larin
Charette AB. * Juteau H. Université de Montréal, Canada
Design of Amphoteric Bifunctional Ligands: Application to the Enantioselective Simmons–Smith Cyclopropanation of Allylic Alcohols.

J. Am. Chem. Soc. 1994;
116: 2651-2652
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Further Information

Publication History

Publication Date:
20 August 2019 (online)

 
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Key words

zinc - cyclopropanation - Simmons–Smith cyclopropanation

Significance

In the paper, Charette and Juteau described a route towards enantioenriched cyclopropanes using a chiral amphoteric bifunctional ligand. This was the first report that enabled efficient chiral cyclopropane synthesis without reliance on covalently bonded chiral auxiliaries.


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Comment

This modification tolerates various functional groups and is highly enantioselective. The chiral ligand could also be recovered through an aqueous extraction at the end of the reaction.


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Reviews

A. B. Charette, J.-F. Marcoux Synlett 1995, 1197–1207; H. Lebel, J.-F. Marcoux, C. Molinaro, A. B. Charette Chem. Rev. 2003, 103, 977–1050.


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