期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 133, 期 39, 页码 15362-15364出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja2079515
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资金
- National Institutes of Health (National Institute of General Medical Sciences) [R01-GM62871]
- Merck Summer Fellowship
- Robert T. Haslam Graduate Fellowship
With the aid of a chiral nickel catalyst, enantioselective gamma- (and delta-) alkylations of carbonyl compounds can be achieved through the coupling of gamma-haloamides with alkylboranes. In addition to primary alkyl nucleophiles, for the first time for an asymmetric cross-coupling of an unactivated alkyl electrophile, an arylmetal, a boronate ester, and a secondary (cyclopropyl) alkylmetal compound are shown to couple with significant enantioselectivity. A mechanistic study indicates that cleavage of the carbon-halogen bond of the electrophile is irreversible under the conditions for asymmetric carbon-carbon bond formation.
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