期刊
ORGANIC LETTERS
卷 13, 期 3, 页码 470-473出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol102818g
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资金
- Kakenhi [21390030, 22106515]
- Grants-in-Aid for Scientific Research [22106515, 21390030] Funding Source: KAKEN
Enantiomerically pure 3'-fluorothalidomide (2) was successfully synthesized by enantiodivergent electrophilic fluorination using a combination of cinchona alkaloids and N-fluorobenzenesulfonimide (NFSI) as the key reaction. Importantly, a single chiral molecule, dihydroquinine (DHQ), allowed access to the mirror image form of 3'-fluorothalidimide by the choice of additives. While the use of TMEDA gave fluorinated (S)-4, the precursor of 2, with 78% ee, Cu(acac)(2)/bipy, afforded the antipode, (R)-4, In 77% ee.
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