Highly diastereoselective Simmons-Smith cyclopropanation of allylic amines.

Org Lett

Department of Chemistry, University of Bristol, Cantock's Close, Bristol, U.K.

Published: November 2003

[reaction: see text] Cyclopropanation of allylic tertiary amines using the Simmons-Smith reagent has been achieved by employing chelating groups in close proximity to the amine. The chelating groups promote cyclopropanation at the expense of N-ylide formation. Using pseudoephedrine as the chelating group, high diastereoselectivity is observed.

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http://dx.doi.org/10.1021/ol035713bDOI Listing

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