期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 3, 页码 775-779出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201308484
关键词
alcohols; chirality; fluoromethylation; stereoselective addition; sulfoximine
资金
- National Basic Research Program of China [2012CB215500, 2012CB821600]
- National Natural Science Foundation of China [20825209, 21372246]
- Chinese Academy of Sciences
- Syngenta PhD Studentship
Although many methods are available for the synthesis of optically enriched monofluoromethyl secondary alcohols, synthesizing optically enriched monofluoromethyl tertiary alcohols remains a challenge. An efficient and easy-to-handle nucleophilic fluoromethylation protocol was developed. The current monofluoromethylation showed much higher facial selectivity than the corresponding difluoromethylation and proceeded via a different type of transition state. Excellent stereoselective control at the fluorinated carbon chiral center was found, an effect believed to be facilitated by the dynamic kinetic resolution of the chiral alpha-fluoro carbanions.
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