Efficient Route to (<i>S</i>)-Azetidine-2-carboxylic Acid
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- FUTAMURA Yasuhiko
- Department of Chemistry, Keio University
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- KUROKAWA Masayuki
- Department of Chemistry, Keio University
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- OBATA Rika
- Department of Chemistry, Keio University
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- NISHIYAMA Shigeru
- Department of Chemistry, Keio University
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- SUGAI Takeshi
- Department of Chemistry, Keio University
書誌事項
- タイトル別名
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- Efficient Route to (S)-Azetidine-2-carboxylic Acid
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説明
A new and efficient route to (S)-azetidine-2-carboxylic acid (>99.9% ee) in five steps and total yield of 48% via malonic ester intermediates was established. As the key step, efficient four-membered ring formation (99%) was achieved from dimethyl (S)-(1′-methyl)benzylaminomalonate by treating with 1,2-dibromoethane (1.5 eq) and cesium carbonate (2 eq) in DMF. Krapcho dealkoxycarbonylation of dimethyl (1′S)-1-(1′-methyl)benzylazetidine-2,2-dicarboxylate, the product of this cyclization procedure, proceeded with preferential formation (2.7:1, 78% total yield) of the desired (2S,1′S)-monoester, with the help of a chiral auxiliary which was introduced on the nitrogen atom. The undesired (2R,1′S)-isomer could be converted to that with proper stereochemistry, by a deprotonation and subsequent re-protonation step. Finally, lipase-catalyzed preferential hydrolysis of the (2S,1′S)-monoester and subsequent deprotection provided enantiomerically pure (S)-azetidine-2-carboxylic acid in a 91% yield from the mixture of (2S,1′S)- and (2R,1′S)-isomers.
収録刊行物
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- Bioscience, Biotechnology, and Biochemistry
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Bioscience, Biotechnology, and Biochemistry 69 (10), 1892-1897, 2005
公益社団法人 日本農芸化学会
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詳細情報 詳細情報について
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- CRID
- 1390282681453056384
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- NII論文ID
- 130000030520
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- NII書誌ID
- AA10824164
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- ISSN
- 13476947
- 09168451
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- NDL書誌ID
- 7678962
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- PubMed
- 16244439
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- 本文言語コード
- en
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- 資料種別
- journal article
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- データソース種別
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- NDLサーチ
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