Enantioselective One-Pot Conjugate Addition of Grignard Reagents to Cyclic Enones Followed by Amidomethylation
The Journal of Organic Chemistry2011Vol. 77(1), pp. 760–765
Citations Over TimeTop 13% of 2011 papers
Abstract
Enantioselective conjugate addition of Grignard reagents to enones, catalyzed by Cu-Taniaphos or Josiphos complex, affords chiral enolates. Ensuing one-pot Mannich reaction with TiCl(4)-generated imine leads to aminocarbonyl compounds with benzyloxycarbonyl-protected nitrogen. Both diastereomers of these compounds are isolated in moderate yields but high enantiomeric purities (up to er 97.5:2.5).
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