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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

Erika M. Vieira, Marc L. Snapper and Amir H. Hoveyda*

*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States, Email:

E. M. Vieira, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc., 2011, 133, 3332-3335.

DOI: 10.1021/ja200311n (free Supporting Information)

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An enantioselective synthesis of homoallylamides through reactions of stable and easily accessible (pinacolato)allylborons with aryl-, heteroaryl-, alkyl-, or alkenyl-substituted N-phosphinoylimines is promoted by 1-5 mol % of readily accessible NHC-Cu complexes, derived from C1-symmetric imidazolinium salts. Allyl additions deliver the desired products in very good yield and enantiomeric ratio.

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Key Words

Homoallylic Amines

ID: J48-Y2011-0560