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

研究成果: Article査読

9 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)718-724
ページ数7
ジャーナルTetrahedron Asymmetry
25
9
DOI
出版ステータスPublished - 2014 5 15

ASJC Scopus subject areas

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

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