期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 133, 期 10, 页码 3332-3335出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja200311n
关键词
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资金
- NIH [GM-57212]
- NSF [DBI-0619576]
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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