Enantioselective Synthesis of Homoallylic Amines through Reactions of (Pinacolato)allylborons with Aryl-, Heteroaryl-, Alkyl-, or Alkene-Substituted Aldimines Catalyzed by Chiral C1-
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- 作者：Erika M. Vieira ; Marc L. Snapper ; Amir H. Hoveyda
- 刊名：Journal of the American Chemical Society
- 出版年：2011
- 出版时间：March 16, 2011
- 年：2011
- 卷：133
- 期：10
- 页码：3332-3335
- 全文大小：810K
- 年卷期：v.133,no.10(March 16, 2011)
- ISSN：1520-5126
文摘
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鈭? mol % of readily accessible NHC鈭扖u complexes, derived from C1-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.