期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 131, 期 20, 页码 6970-+出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja902205f
关键词
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资金
- NSERC (Canada)
- Canada Research Chair Program
- Universite de Montreal
- Financiere Manuvie
- NSERC (USRA)
A highly stereoselective (up to 98% ee and 99:1 dr) Rh(II)-catalyzed formation of nitrile-substituted cyclopropanes is described. alpha-Cyano diazoacetamide reagents react with a variety of mono- and disubstituted olefins in good yields and excellent enantio- and diastereocontrol. Less reactive substrates, such as aliphatic olefins, also undergo the reaction. This new methodology features the unprecedented use of an achiral, hydrogen-bond donor additive to enhance the selectivity and exploits the powerful trans-directing ability of amides solving the diastereocontrol issue of the formation of substituted 1-cyanocyclopropane-1-carboxy derivatives.
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