4.8 Article

Brine-Stabilized 2,2,2-Trifluorodiazoethane and Its Application in the Synthesis of CF3-Substituted Cyclopropane α-Amino Acids

Journal

ORGANIC LETTERS
Volume 17, Issue 14, Pages 3442-3445

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b01450

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Funding

  1. National Natural Science Foundation of China
  2. National Basic Research Program of China (973 Program) [2014CB745100]
  3. Tianjin Municipal Science & Technology Commission [14JCZDJC33400]

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A facile thermodynamic cyclopropanation of trisubstituted olefinic azlactone with a stock solution of CF3CHN2 in CH3CN is realized. This method shows excellent generality, affording a wide range of trifluoromethyl-substituted cyclopropanes bearing azlactone rings in good to high yields and diastereoselectivities. With the products in hand, the trifluoromethyl-substituted cyclopropane alpha-amino acids and relative peptide derivatives could be readily obtained.

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