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

Masayuki Kurokawa, Takeshi Sugai

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1021-1025
Number of pages5
JournalBulletin of the Chemical Society of Japan
Volume77
Issue number5
DOIs
Publication statusPublished - 2004 May 1

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'Both enantiomers of N-Boc-indoline-2-carboxylic esters'. Together they form a unique fingerprint.

  • Cite this