The solid-state structure of (+)-(i)-menthyl 2-formamido-4, 4,4-trifluorobutanoate and the hydrogenation of the 2-butenoate precursor

Robert Glaser, Shimona Geresh, Shlomo Luria, Marc Drouin, André Michel

Research output: Contribution to journalArticlepeer-review

Abstract

Hydrogenation of Z-(-)-(1′R, 3′R, 4′S)-menthyl 2-formamido-4,4,4-trifluoro-2-butenoate catalyzed by Pd/C was performed at atmospheric pressure to yield a mixture of (2R, 1′R, 3′R, 4′S)- and (2 S, 1′R, 3′R, 4′S)-menthyl 2-formamido-4,4,4-trifluorobutanoate diastereomers in a 55:45 ratio, respectively. Repeated fractional crystallization from ethyl acetate and vapor diffusion of petroleum ether afforded (+)-(2 S, 1′R, 3′R, 4′S)-menthyl 2-formamido-4,4,4-trifluorobutanoate as clear colorless, crystalline prisms which were subjected to single-crystal X-ray diffraction analysis. The crystals belong to the orthorhombic system P212121, and at 213 K:a=5.054(1), b= 10.000(2), c=32.707(1) Å, V=1652.9(4) Å3, Z=4, R(F)=0.040, and Rw(F)=0.037. The finding of the (2 S)-configuration for the formamido-acid portion of the (+)-ester enabled the configurational assignment of the asymmetric hydrogenation products of Z-methyl 2-formamido-4, 4,4-trifluoro-2-butenoate catalyzed by chiral diphosphine/rhodium(I) complexes.

Original languageEnglish
Pages (from-to)277-282
Number of pages6
JournalStructural Chemistry
Volume5
Issue number4
DOIs
StatePublished - 1 Aug 1994

Keywords

  • Stereochemistry
  • X-ray crystallography
  • asymmetric hydrogenation
  • configuration

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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