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 journalArticlepeer-review

23 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 (-)-cannabispirenones A and B. Art and crafts: Intramolecular Friedel-Crafts-type 1,4-addition under organocatalytic conditions enabled the highly enantioselective construction of spiroindanes containing an all-carbon quaternary stereocenter. The reaction was applied to the asymmetric formal synthesis of the spirocyclic natural products (-)-cannabispirenone A and B (see scheme).

Original languageEnglish
Pages (from-to)6734-6738
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number23
DOIs
Publication statusPublished - 2016 Jun 1

Keywords

  • asymmetric catalysis
  • cyclization
  • natural products
  • organocatalysis
  • spiro compounds

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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