Preparation of chiral building blocks for the enantioselective total synthesis of ent-kauranoids by the pig liver esterase-catalyzed asymmetric hydrolysis of a dialkyl malonate-type prochiral diester

Yuji Namiki, Tomohiro Fujii, Masahisa Nakada

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The preparation of chiral building blocks, suitable for use in the enantioselective total synthesis of kauranoids and ent-kauranoids, is reported herein. The pig liver esterase-catalyzed asymmetric hydrolysis of dimethyl 3,3-dimethyl-2-methylenecyclohexane-1,2-dicarboxylate, a malonate-type prochiral diester, afforded the corresponding half-ester in 96% yield and with 99% enantiomeric excess. The absolute configuration of the half-ester was determined by X-ray crystallographic analysis of its derivative and its enantiodivergent transformations are also described herein.

Original languageEnglish
Pages (from-to)718-724
Number of pages7
JournalTetrahedron Asymmetry
Volume25
Issue number9
DOIs
Publication statusPublished - 2014 May 15

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ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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