Stereoselective double alkylation of the acetoacetate ester α-carbon on a D-glucose-derived template: Application to the synthesis of enantiopure cycloalkenones bearing an asymmetric quaternary carbon

Ikuko Kozawa, Yoko Akashi, Kumiko Takiguchi, Daisuke Sasaki, Daisuke Sawamoto, Ken Ichi Takao, Kin Ichi Tadano

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

The previously developed D-glucose derivative, i.e., methyl 6-deoxy-2,3-di-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside, served as a significant stereocontrolling element for the diastereoselective alkylation of the α-carbon in its acetoacetate at C-4 with two types of alkyl halides. The thus obtained doubly alkylated acetoacetate moiety bearing both methyl and allyl groups was efficiently converted into functionalized cycloalk-2-en-1-one derivatives by means of an intramolecular aldol strategy. Furthermore, the synthetic utility of the cycloalkenones was exemplified through the 1,4-addition to the thus obtained cyclopentenone derivative.

Original languageEnglish
Pages (from-to)399-402
Number of pages4
JournalSynlett
Issue number3
DOIs
Publication statusPublished - 2007 Feb 15

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Keywords

  • Asymmetric quaternization
  • Chiral auxiliary
  • D-glucose derivatives
  • Double alkylation
  • Intramolecular aldol reactions

ASJC Scopus subject areas

  • Organic Chemistry

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