脱水縮合を伴う速度論的光学分割反応の開発

• 椎名 勇

  東京理科大学理学部応用化学科

• 中田 健也

  島根大学大学院総合理工学研究科

書誌事項

タイトル別名

• Development of Kinetic Resolution of Racemic Alcohols and Carboxylic Acids Accompanied with Dehydration Condensation
• ダッスイ シュクゴウ オ トモナウ ソクドロンテキ コウガク ブンカツ ハンノウ ノ カイハツ

抄録

A novel and efficient method for the kinetic resolution of racemic alcohols with achiral carboxylic acids or racemic carboxylic acids with achiral alcohols using dehydration condensation is accounted in this paper. The first kinetic resolution of racemic alcohols with achiral carboxylic acids was accomplished by asymmetric esterification via the in situ formation of a mixed anhydride using carboxylic anhydrides as coupling reagents in the presence of chiral acyl-transfer catalysts. Because this protocol utilized the transacylation process to generate the mixed-anhydride, not only racemic secondary alcohols but also racemic carboxylic acids are applicable to the asymmetric esterification in the same manner. The variety of optically active carboxylic esters are also produced by the kinetic resolution of racemic 2-arylalkanoic acids, including non-steroidal anti-inflammatory drugs (NSAIDs), with achiral alcohols, using carboxylic anhydrides in the presence of chiral acyl-transfer catalysts.

収録刊行物

• 有機合成化学協会誌

  有機合成化学協会誌 72 (8), 919-928, 2014

  公益社団法人 有機合成化学協会

キーワード

• kinetic resolution
• asymmetric esterification
• mixed-anhydride method
• carboxylic anhydride
• dehydration condensation
• organocatalysis
• tetramisole derivative
• carboxylic ester
• carboxylic acid
• non-steroidal anti-inflammatory drug

詳細情報

• CRID: 1390282680316147200
• NII論文ID: 130004691492
• NII書誌ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.72.919
• ISSN: 18836526
• ISSN: 00379980
• NDL書誌ID: 025750318
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I025750318
• 本文言語コード: ja
• データソース種別:
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