シス-2-フルオロシクロプロパンカルボン酸の立体選択的な合成
書誌事項
- タイトル別名
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- Stereoselective Synthesis of cis-2-Fluorocyclopropanecarboxylic Acid
説明
cis-2-Fluorocyclopropanecarboxylic acid (cis-FCpCA) is a key intermediate for the synthesis of an antibacterial agent Sitafloxacin, therefore many synthetic efforts for the synthesis of dl-cis-FCpCA have been reported so far. We herein report an efficient stereoselective synthesis of dl-cis-FCpCA. The strategy for the synthesis of dl-cis-FCpCA derives from employment of stereoselective rhodium-catalyzed cyclopropanation reaction of (1-fluorovinylsulfonyl)benzene (1) with diazo esters 2. The cyclopropanation reaction of 1 with tert-butyl diazoacetate catalyzed by [Rh(O2CCPh3)2]2 proceeded stereoselectively to the desired tert-butyl trans-2-fluoro-2-phenylsulfonylcyclopropane carboxylate (trans-3, R = tert-Bu) in an 80% yield (trans:cis = 93:7). The synthesis of dl-cis-FCpCA was completed by reductive cleavage of a phenylsulfonyl group of trans-3 and subsequent hydrolysis of an ester group.
収録刊行物
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- 反応と合成の進歩シンポジウム 発表要旨概要
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反応と合成の進歩シンポジウム 発表要旨概要 34 (0), 13-13, 2008
日本薬学会化学系薬学部会
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詳細情報 詳細情報について
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- CRID
- 1390282680612882304
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- NII論文ID
- 130006998846
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- 本文言語コード
- ja
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- データソース種別
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- JaLC
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可
