2008年5月
Efficient synthesis of trifluoromethyl and related trisubstituted alkene dipeptide isosteres by palladium-catalyzed carbonylation of amino acid derived allylic carbonates
JOURNAL OF ORGANIC CHEMISTRY
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- 巻
- 73
- 号
- 10
- 開始ページ
- 3942
- 終了ページ
- 3945
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1021/jo702318d
- 出版者・発行元
- AMER CHEMICAL SOC
A novel stereoselective synthetic approach to (Z)-trifluoromethylalkene dipeptide isosteres (CF(3)-ADIs) is described. Starting from readily available N-BOC-L-phenylalanine, Phe-Gly type CF(3)-ADIs were obtained through palladium-catalyzed carbonylation of allylic carbonates under CO. While the reaction of N-Boc derivatives proceeds in excellent yields but lower stereoselectivity (E:Z = 62:38-43:57), the reaction of the NN-diBoc derivative exclusively affords the desired (Z)-isomer in 61% yield. We also present a highly stereoselective synthesis of several Phe-Gly type trisubstituted alkene dipeptide isosteres by palladium-catalyzed carbonylation.
- リンク情報
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- DOI
- https://doi.org/10.1021/jo702318d
- J-GLOBAL
- https://jglobal.jst.go.jp/detail?JGLOBAL_ID=200902241093443569
- PubMed
- https://www.ncbi.nlm.nih.gov/pubmed/18412390
- Web of Science
- https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000255698500043&DestApp=WOS_CPL
- ID情報
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- DOI : 10.1021/jo702318d
- ISSN : 0022-3263
- J-Global ID : 200902241093443569
- PubMed ID : 18412390
- Web of Science ID : WOS:000255698500043