Asymmetric catalysis on the intramolecular cyclopropanation of α-Diazo-β-keto sulfones

Masahiro Honma, Takashi Sawada, Yuri Fujisawa, Masayuki Utsugi, Hideaki Watanabe, Akinori Umino, Takehiko Matsumura, Takayuki Hagihara, Masashi Takano, Masahisa Nakada

Research output: Contribution to journalArticle

114 Citations (Scopus)

Abstract

This work describes the development of a highly enantioselective asymmetric catalysis on the intramolecular cyclopropanation of α-diazo-β-keto sulfones. We have found that the catalytic asymmetric intramolecular reactions of α-diazo-β-keto sulfones generally proceed with high enantioselectivity when the α-diazo-β-keto mesityl sulfone is used with the newly prepared ligand 2e. The absolute configuration of products has been determined by X-ray crystallographic analysis, and the outcome of the enantioselectivities is explained well by our proposed models A and B. The products possess great potential for natural product synthesis because (1) many different chemistries of cyclopropane, ketone, and sulfone are available, and (2) the products are generally highly crystalline, facilitating the supplies of enantiomerically pure synthetic intermediates.

Original languageEnglish
Pages (from-to)2860-2861
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number10
DOIs
Publication statusPublished - 2003 Mar 12

    Fingerprint

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Honma, M., Sawada, T., Fujisawa, Y., Utsugi, M., Watanabe, H., Umino, A., Matsumura, T., Hagihara, T., Takano, M., & Nakada, M. (2003). Asymmetric catalysis on the intramolecular cyclopropanation of α-Diazo-β-keto sulfones. Journal of the American Chemical Society, 125(10), 2860-2861. https://doi.org/10.1021/ja029534l