期刊
SCIENCE
卷 353, 期 6294, 页码 51-54出版社
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.aaf8078
关键词
-
资金
- NIH [GM043214]
- NSF
Difluoromethyl groups possess specific steric and electronic properties that invite their use as chemically inert surrogates of alcohols, thiols, and other polar functional groups important in a wide assortment of molecular recognition processes. We report here a method for the catalytic, asymmetric, migratory geminal difluorination of beta-substituted styrenes to access a variety of products bearing difluoromethylated tertiary or quaternary stereocenters. The reaction uses commercially available reagents (m-chloroperbenzoic acid and hydrogen fluoride pyridine) and a simple chiral aryl iodide catalyst and is carried out readily on a gram scale. Substituent effects and temperature-dependent variations in enantioselectivity suggest that cation-p interactions play an important role in stereodifferentiation by the catalyst.
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