Studies on the structure-enantioselectivity relationships in the catalytic asymmetric intramolecular cyclopropanation reaction of α-diazo-β-keto sulfones possessing a methyl-substituted phenyl group

Hiroyuki Takeda, Masahisa Nakada

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26 Citations (Scopus)

Abstract

This manuscript describes studies on structure-enantioselectivity relationships in the catalytic asymmetric intramolecular cyclopropanation (IMCP) reaction of α-diazo-β-keto sulfones possessing a methyl-substituted phenyl group. Enantioselectivity of the IMCP reaction of the α-diazo-β-keto sulfones was varied by the position of a methyl group on the phenyl group in the substrate, and the 2,3-dimethylphenyl sulfone 11h provided the product 12h in 95% yield with 93% ee. This yield is superior to that of the substrate with a mesityl sulfone 11b, and the product 12h is useful because alkylation of its cyclopropane-opened β-keto sulfone derivative 15h provides the C-alkylated product as a major product.

Original languageEnglish
Pages (from-to)2896-2906
Number of pages11
JournalTetrahedron Asymmetry
Volume17
Issue number20
DOIs
Publication statusPublished - 2006 Nov 6

ASJC Scopus subject areas

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

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