Optical Resolution and Epimerization of Fluorosilane Having an Optically Active Amino Group: A New, Convenient Access to Optically Active Silicon Compounds

Atsushi Kawachi, Hirofumi Maeda, Koichi Mitsudo, Kohei Tamao

Research output: Contribution to journalArticlepeer-review

23 Citations (Scopus)

Abstract

The diastereomeric (amino)fluorosilane 2 is prepared from the prochiral (1-naphthyl)-phenyldifluorosilane 5 with optically active bis[(R)-1-phenylethyl]amine (3). The two isomers of 2 can be easily separated due to their large solubility difference in CH3NO2. In addition, 2 undergoes epimerization at the silicon atom in the presence of a catalytic amount of AgF. Stereospecific methylation and the deamination-fluorination of 2 give the enantiomerically pure (1-naphthyl)phenylmethylfluorosilane (1).

Original languageEnglish
Pages (from-to)4530-4533
Number of pages4
JournalOrganometallics
Volume18
Issue number22
DOIs
Publication statusPublished - Oct 25 1999
Externally publishedYes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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