Diastereo-Face Selectivity in the Aldol Reaction of Boryl Enolate Derived from Oppolzer′s Sultam
書誌事項
- タイトル別名
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- Diastereo-Face Selectivity in the Aldol Reaction of Boryl Enolate Derived from Oppolzer's Sultam.
- Diastereo-Face Selectivity in the Aldol
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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).
収録刊行物
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- ＣＨＥＭＩＣＡＬ ＆ ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ ＢＵＬＬＥＴＩＮ
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ＣＨＥＭＩＣＡＬ ＆ ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ ＢＵＬＬＥＴＩＮ 44 (11), 2003-2008, 1996
公益社団法人 日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1390001204160281984
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- NII論文ID
- 130003947040
- 110003631805
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- NII書誌ID
- AA00602100
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- COI
- 1:CAS:528:DyaK28Xnt1yjsbs%3D
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- ISSN
- 13475223
- 00092363
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- NDL書誌ID
- 4079992
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可
