Asymmetric transformation of 2-phenyl- and 2-chloroalkanoic acids via chiral oxazolines.

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概要

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• Asymmetric transformation of racemic 2-phenyl- and 2-chloroalkanoic acids <I>via</I> oxazolines into the corresponding optically active acids was investigated using (<I>S</I>)-phenylalaninol as a chiral auxiliary. The asymmetric transformation was performed by metalation of the oxazolines with butyllithium followed by protonation of the resulting lithiooxazolines. 2-Phenyl- and 2-chloroalkanoic acids were obtained in the optical yields of 29–53% and 45–73%, respectively, by the acidic hydrolysis of the chiral oxazolines thus formed. The mechanism of the asymmetric transformation was discussed.

• 公益社団法人 日本化学会の論文

著者

• Noguchi Masao

  Central Research Institute The Japan Tobacco & Salt Public Corporation

• MATSUSHITA Hajime

  Central Research Institute, Japan Tobacco Inc.

• Yoshikawa Sadao

  Department Of Applied Chemistry Faculty Of Science And Technology Keio University

• SHIBATA Saizo

  Central Pharmaceutical Research Institute, Japan Tobacco Inc.

• Kaneko Hajime

  Central Research Institute Japan Tobacco Inc.

• Saburi Masahiko

  Department Of Applied Chemistry Saitama Institute Of Technology

• Matsushita Hajime

  Central Research Institute, The Japan Tobacco and Salt Public Corporation

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