期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 132, 期 31, 页码 10630-10633出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja104777u
关键词
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资金
- NIH [GM-57212]
- NSF [CHE-0715138, DBI-0619576]
A Cu-catalyzed method for enantioselective boronate conjugate additions to trisubstituted alkenes of acyclic alpha,beta-unsaturated carboxylic esters, ketones, and thioesters is disclosed. All transformations are promoted by 5 mol % of a chiral monodentate NHC-Cu complex, derived from a readily available C(1)-symmetric imidazolinium salt, and in the presence of commercially available bis(pinacolato)diboron. Reactions are efficient (typically, 60% to >98% yield after purification) and deliver the desired beta-boryl carbonyls in up to >98:2 enantiomer ratio (er). Processes involving unsaturated thioesters proceed with higher enantioselectivity (vs carboxylic esters or ketones), and the resulting products can be functionalized by Ag-mediated or Pd-catalyzed reactions that furnish the derived carboxylic ester or various ketones. Routine oxidation affords beta-hydroxy ketones or carboxylic esters, ketone aldol products that cannot be otherwise prepared efficiently by an alternative catalytic enantioselective protocol.
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