Both enantiomers of N-Boc-indoline-2-carboxylic esters

Masayuki Kurokawa, Takeshi Sugai

研究成果: Article査読

19 被引用数 (Scopus)

抄録

An immobilized form of Candida antarctica lipase (Chirazyme L-2) catalyzed enantioselective hydrolysis (E > 1000) of N-Boc-indoline-2-carboxylic acid methyl ester. The reaction proceeded efficiently at 60 °C, a temperature over the melting point of substrate, in the conversion of 49.9% to provide the hydrolyzed product, (S)-carboxylic acid with >99.9% ee and the unreacted (R)-ester with 99.6% ee. A newly developed expeditious route to the racemic substrate (a total of six steps, 60% yield), starting from aniline and ethyl α-methylacetoacetate, established the scalable chemoenzymatic synthesis of the desired compounds in both enantiomerically pure forms.

本文言語English
ページ(範囲)1021-1025
ページ数5
ジャーナルBulletin of the Chemical Society of Japan
77
5
DOI
出版ステータスPublished - 2004 5月 1

ASJC Scopus subject areas

  • 化学 (全般)

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