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

11 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

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AU - Sawamoto, Daisuke

AU - Takao, Kenichi

AU - Tadano, Kin Ichi

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