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 |
| Publication status | Published - Oct 25 1999 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Inorganic Chemistry
- Organic Chemistry
Cite this
Optical Resolution and Epimerization of Fluorosilane Having an Optically Active Amino Group : A New, Convenient Access to Optically Active Silicon Compounds. / Kawachi, Atsushi; Maeda, Hirofumi; Mitsudo, Koichi; Tamao, Kohei.
In: Organometallics, Vol. 18, No. 22, 25.10.1999, p. 4530-4533.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Optical Resolution and Epimerization of Fluorosilane Having an Optically Active Amino Group
T2 - A New, Convenient Access to Optically Active Silicon Compounds
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).
UR - http://www.scopus.com/inward/record.url?scp=0001521004&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0001521004&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0001521004
VL - 18
SP - 4530
EP - 4533
JO - Organometallics
JF - Organometallics
SN - 0276-7333
IS - 22
ER -