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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.


 

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.


 

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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