4.7 Article

Achieving regio- and stereo-control in the fluorination of aziridines under acidic conditions

期刊

CHEMICAL COMMUNICATIONS
卷 52, 期 91, 页码 13353-13356

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/c6cc07855a

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资金

  1. National Institutes of Health [R15 GM101604-01]
  2. National Science Foundation [CHE-1401700]
  3. National Science Foundation of China [NSFC-21472018]
  4. Sao Paulo Research Foundation (FAPESP) [2015/08541-6]
  5. Division Of Chemistry
  6. Direct For Mathematical & Physical Scien [1401700] Funding Source: National Science Foundation

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We developed an efficient fluorination protocol that converts easily accessible aziridines into beta-fluoroamines, which are important motifs in biologically active molecules. In contrast with traditional fluorination approaches, DMPU-HF has shown both higher reactivity and regioselectivity and good functional group tolerance; thus, a wide scope of beta-fluoroamines can now be accessed conveniently. The stereochemical behavior of the ring opening depends on the substitution pattern of the aziridine substrate.

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