Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Diastereo-Face Selectivity in the Aldol Reaction of Boryl Enolate Derived from Oppolzer's Sultam
Katsuhiko ISEKISatoshi OISHIYoshiro KOBAYASHI
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1996 年 44 巻 11 号 p. 2003-2008

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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).
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© The Pharmaceutical Society of Japan
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