Diastereo-Face Selectivity in the Aldol Reaction of Boryl Enolate Derived from Oppolzer's Sultam
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概要
- 論文の詳細を見る
In the Oppolzer aldol reaction, aldehyde reacts exclusively on the Si face (C(α)-Si attack) of the double bond of the boryl enolate 2 derived from (1S, 2R)-N-propionylbornane-10,2-sultam (1), providing only 3a stereoselectively. Hexafluoroacetone (4) caused complete reversal of the diastereo-face selectivity, reacting exclusively on the Re face (C(α)-Re attack) of 2 to give only 5. Trifluoroacetaldehyde (8) and 2,2-difluoro-5-phenylpentanal (9) caused partial reversal of the diastereo-face selectivity, giving significant amounts of unexpected and unusual syn- (12c, 13c) and anti- (12d, 13d) aldols along with the normal syn-aldol (12a, 13a). This finding was applied to the reactions of the boryl enolate with phenylglyoxal (10) and ethyl glyoxylate (11).
- 公益社団法人日本薬学会の論文
- 1996-11-15
著者
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大石 訓司
Daikin Industries, Ltd.,
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Yasui Koichiro
Molecular Gastroenterology And Hepatology Kyoto Prefectural University Of Medicine Graduate School O
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Yasui Kohichiroh
Molecular Gastroenterology And Hepatology Kyoto Prefectural University Of Medicine Graduate School O
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Kobayashi Yoshiharu
Tokyo University of Pharmacy and Life Science
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ISEKI Katsuhiko
MEC Laboratory, Daikin Industries, Ltd.
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OISHI Satoshi
MEC Laboratory, Daikin Industries, Ltd.
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KOBAYASHI Yoshiro
MEC Laboratory, Daikin Industries, Ltd.
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Iseki K
Mec Laboratory Daikin Industries Ltd.
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Oishi S
Mec Laboratory Daikin Industries Ltd.
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大石 訓司
Daikin Industries Ltd.
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Yoshida Kyotaro
Dep. Of Medical Biochemistry Kobe Pharmaceutical Univ.
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