期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 133, 期 23, 页码 8972-8981出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja201237j
关键词
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资金
- Natural Science and Engineering Research Council of Canada (NSERC)
- Canada Foundation for Innovation
- Canada Research Chair Program
- Centre in Green Chemistry and Catalysis (CGCC)
- Universite de Montreal
- NSERC (PGS D)
Different diacceptor diazo compounds bearing an alpha-PMP-ketone group were found to be effective carbene precursors for the highly stereoselective Rh-2(S-TCPTTL)(4)-catalyzed cyclopropanation of alkenes (EWG = NO2, CN, CO2Me). The resulting products were readily transformed into a variety of biologically relevant enantiopure molecules, such as cyclopropane alpha- and beta-amino acid derivatives. Different mechanistic studies carried out led to a rationale for the high diastereo- and enantioselectivity obtained, where the PMP-ketone moiety was found to play a critical role in the stereoinduction process. Additionally, the use of catalytic amounts of achiral Lewis bases to influence the enantioinduction of the reactions developed is documented.
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