Stereoselective carbon-carbon bond forming reactions of chiral cyclopent-2-enone and cyclopentene-1-methanol, both spiro-connecting a 1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl ring

Ken Ichi Takao, Hiroshi Saegusa, Gohshi Watanabe, Kin Ichi Tadano

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The conjugate additions of a variety of organocopper reagents or dimethyl malonate anion to a spirocyclic cyclopent-2-enone connecting a 1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl ring as a constituent of the spiro structure, namely (1S,3R,4R,5R)-3,4-(isopropylidenedioxy)-1-[(1R)-1,2-(isopropylidenedioxy)ethyl]-2-oxa-spiro[4.4]non-6-en-8-one, proceeded stereoselectively in some cases affording a variety of β-functionalized cyclopentanone derivatives. The thermal treatment of (1S,3R,4R,5R)-7-(hydroxymethyl)-3,4-(isopropylidenedioxy)-1-[(1R)-1,2-(isopropylidenedioxy)ethyl]-2-oxaspiro[4.4]non-6-ene, another D-glucose-derived spirocyclic substrate, with triethyl orthoacetate in the presence of a catalytic amount of acid afforded the Claisen rearrangement product with a high level of diastereoselectivity. Copyright (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)453-464
Number of pages12
JournalTetrahedron Asymmetry
Volume11
Issue number2
DOIs
Publication statusPublished - 2000 Feb 11

ASJC Scopus subject areas

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

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