Development of catalytic asymmetric intramolecular cyclopropanation of α-diazo-β-keto sulfones and applications to natural product synthesis

Masahiro Honma, Hiroyuki Takeda, Masashi Takano, Masahisa Nakada

Research output: Contribution to journalReview article

41 Citations (Scopus)

Abstract

The catalytic asymmetric intramolecular cyclopropanation (CAIMCP) of α-diazo-β-keto sulfones developed in our laboratory and applications to the total synthesis of natural products are described. CAIMCP features (a) a wide applicability, not only to the preparation of bicyclo[n.1.0]alkanes and tricyclo[4.n.0.0]alkenes, but also to the enantioselective total synthesis of natural products, (b) the formation of highly crystalline products, which facilitate the production of enantiomerically pure synthetic intermediates, and (c) the generation of products with a variety of functionalities, such as cyclopropane, ketone, and sulfone, beneficial to the total synthesis of natural products.

Original languageEnglish
Pages (from-to)1695-1712
Number of pages18
JournalSynlett
Issue number11
DOIs
Publication statusPublished - 2009 Jul 1

Keywords

  • Asymmetric catalysis
  • Carbene complexes
  • Diazo compounds
  • Natural products
  • Sulfones

ASJC Scopus subject areas

  • Organic Chemistry

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