Enantioselective Synthesis of Homoallylic Amines Through Reactions of (pinacolato)allylborons with Aryl-, Heteroaryl-, Alkyl-, or Alkene-substituted Aldimines Catalyzed by Chiral C1-symmetric NHC-Cu Complexes

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2011 Feb 24

PMID 21341657

Citations 26

Authors

Erika M Vieira

Marc L Snapper

Amir H Hoveyda

Affiliations

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Abstract

A catalytic method for enantioselective synthesis of homoallylamides through Cu-catalyzed reactions of stable and easily accessible (pinacolato)allylborons with aryl-, heteroaryl-, alkyl-, or alkenyl-substituted N-phosphinoylimines is disclosed. Transformations are promoted by 1-5 mol % of readily accessible NHC-Cu complexes, derived from C(1)-symmetric imidazolinium salts, which can be prepared in multigram quantities in four steps from commercially available materials. Allyl additions deliver the desired products in up to quantitative yield and 98.5:1.5 enantiomeric ratio and are amenable to gram-scale operations. A mechanistic model accounting for the observed selectivity levels and trends is proposed.

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