Carbocyclic Amino Ketones by Bredt's Rule-Arrested Kulinkovich-de Meijere Reaction.

Angew Chem Int Ed Engl

Department of Chemistry, Temple University, 1901 N. 13th St., Philadelphia, PA, 19122, USA.

Published: February 2016

The Ti(II) -mediated formation of cyclopropylamines from alkenes and amides, the Kulinkovich-de Meijere reaction, involves two carbon-carbon bond-forming steps. Strategic use of a tricyclic intermediate can arrest the process if the second step requires formation of a bridgehead double bond. Use of this Bredt's rule constraint results in the production of carbocyclic amino ketones, key alkaloid building blocks.

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http://dx.doi.org/10.1002/anie.201509983DOI Listing

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