Enantioselective Organocatalytic Construction of Spiroindane Derivatives by Intramolecular Friedel-Crafts-Type 1,4-Addition

Keisuke Yoshida, Yukihiro Itatsu, Yuta Fujino, Hiroki Inoue, Ken ichi Takao

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

The highly enantioselective organocatalytic construction of spiroindanes containing an all-carbon quaternary stereocenter by intramolecular Friedel-Crafts-type 1,4-addition is described. The reaction was catalyzed by a cinchonidine-based primary amine and accelerated by water and p-bromophenol. A variety of spiro compounds containing quaternary stereocenters were obtained with excellent enantioselectivity (up to 95%ee). The reaction was applied to the asymmetric formal synthesis of the spirocyclic natural products (-)-cannabispirenonesA and B.

Original languageEnglish
JournalAngewandte Chemie - International Edition
DOIs
Publication statusAccepted/In press - 2016

Keywords

  • Asymmetric catalysis
  • Cyclization
  • Natural products
  • Organocatalysis
  • Spiro compounds

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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