Chiral silver phosphate catalyzed transformation of ortho-alkynylaryl ketones into 1H-isochromene derivatives through an intramolecular-cyclization/ enantioselective-reduction sequence

Masahiro Terada, Feng Li, Yasunori Toda

Research output: Contribution to journalArticlepeer-review

87 Citations (Scopus)

Abstract

The transformation of ortho-alkynylaryl ketones through a cyclization/enantioselective-reduction sequence in the presence of a chiral silver phosphate catalyst afforded 1H-isochromene derivatives in high yield with fairly good to high enantioselectivity. An asymmetric synthesis of the 9-oxabicyclo[3.3.1]nona-2,6-diene framework, which has been found in some biologically active molecules, is presented as a demonstration of the synthetic utility of this method. Dependent on its other half: The title reaction of ortho-alkynylaryl ketones in the presence of a silver catalyst with a chiral counteranion afforded 1H-isochromene derivatives in high yield with good to high enantioselectivity (see scheme; R1=alkyl, aryl; R2=aryl; R3=H, F). An asymmetric synthesis of the 9-oxabicyclo[3.3.1]nona-2,6- diene framework found in biologically active molecules highlights the synthetic utility of this method.

Original languageEnglish
Pages (from-to)235-239
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number1
DOIs
Publication statusPublished - 2014 Jan 3

Keywords

  • asymmetric catalysis
  • cyclization
  • enantioselective reduction
  • isobenzopyrylium ions
  • silver salts

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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