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, Kenichi 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

Fingerprint

Bearings (structural)
Alkylation
Esters
Carbon
Derivatives
Glucose
acetoacetic acid

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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. / Kozawa, Ikuko; Akashi, Yoko; Takiguchi, Kumiko; Sasaki, Daisuke; Sawamoto, Daisuke; Takao, Kenichi; Tadano, Kin Ichi.

In: Synlett, No. 3, 15.02.2007, p. 399-402.

Research output: Contribution to journalArticle

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AU - Kozawa, Ikuko

AU - Akashi, Yoko

AU - Takiguchi, Kumiko

AU - Sasaki, Daisuke

AU - Sawamoto, Daisuke

AU - Takao, Kenichi

AU - Tadano, Kin Ichi

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