通过狄尔斯-阿尔德反应对映选择性地构建氟甲基化的手性碳中心。
A Diels-Alder approach to the enantioselective construction of fluoromethylated stereogenic carbon centers.
机构信息
Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Hibarigaoka, Toyohashi 441-8580, Japan.
出版信息
Chem Commun (Camb). 2012 Jan 11;48(3):413-5. doi: 10.1039/c1cc15889a. Epub 2011 Nov 11.
PMID:22075652
Abstract
Highly enantioselective Diels-Alder reactions of β-fluoromethylacrylates were carried out in the presence of a Lewis acid activated chiral oxazaborolidine catalyst. These reactions yielded fluoromethylated cyclohexenes, including trifluoromethyl-, difluoromethyl-, and monofluoromethyl cyclohexenes, as nearly pure enantiomers. The resulting fluoromethyl cyclohexenes were converted into potential synthetic intermediates for bioactive compounds.
摘要
在路易斯酸活化的手性噁唑硼烷催化剂存在下，β-氟甲基丙烯酸酯进行了高对映选择性的 Diels-Alder 反应。这些反应生成了氟甲基环己烯，包括三氟甲基、二氟甲基和一氟甲基环己烯，几乎为纯对映异构体。得到的氟甲基环己烯被转化为生物活性化合物的潜在合成中间体。
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