期刊
CHINESE JOURNAL OF ORGANIC CHEMISTRY
卷 38, 期 6, 页码 1525-1529出版社
SCIENCE PRESS
DOI: 10.6023/cjoc201712020
关键词
CH fluorination; organofluorine; amino acid
资金
- National Natural Science Foundation of China [21502076]
- Outstanding Young Talents Scheme of Jiangxi Province [20171BCB23039]
Benzylic CH fluorination has emerged as a valuable tool for the introduction of fluorine. However, the power-fulness of benzylic CH fluorination has not been tested in any multi-step synthesis alpha beta-Difluoro-gamma-amino acids are useful entities for biological application owing to the so-called fluorine conformational effect. In this work, benzylic CH fluorination has been successfully utilized as the key step for the formal synthesis of syn-alpha,beta-difluoro-gamma-amino acid 1, a very challenging but useful target. The approach developed in this work could be viewed as more practical compared to the previous one, because: (1) no corrosive and toxic nucleophilic fluorinating reagents are used, (2) the overall yield is 18% (the previous approach is about 5%), and (3) the key benzylic CH reaction developed by Chen and co-workers was scaled up to one gram without decreasing its original efficiency. A staking fluorine effect was observed: a carbon with one fluorine atom on the adjacent carbon is much less reactive than an ordinary carbon for the benzylic CH fluorination.
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