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

doi:10.1021/om9904394

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 journal › Article › peer-review

25 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 language	English
Pages (from-to)	4530-4533
Number of pages	4
Journal	Organometallics
Volume	18
Issue number	22
DOIs	https://doi.org/10.1021/om9904394
Publication status	Published - Oct 25 1999
Externally published	Yes

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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

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).",

author = "Atsushi Kawachi and Hirofumi Maeda and Koichi Mitsudo and Kohei Tamao",

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AU - Kawachi, Atsushi

AU - Maeda, Hirofumi

AU - Mitsudo, Koichi

AU - Tamao, Kohei

PY - 1999/10/25

Y1 - 1999/10/25

N2 - 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).

AB - 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).

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

Abstract

ASJC Scopus subject areas

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