Enantio- and diastereoselective access to distant stereocenters embedded within tetrahydroxanthenes: Utilizing ortho-quinone methides as reactive intermediates in asymmetric brønsted acid catalysis

Chien Chi Hsiao, Hsuan Hung Liao, Magnus Rueping*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

168 Scopus citations

Abstract

A protocol for the highly enantioselective synthesis of 9-substituted tetrahydroxanthenones by means of asymmetric Brønsted acid catalysis has been developed. A chiral binolbased N-triflyphosphoramide was found to promote the in situ generation of ortho-quinone methides and their subsequent reaction with 1,3-cyclohexanedione to provide the desired products with excellent enantioselectivities. In addition, a highly enantio- and diastereoselective Brønsted acid catalyzed desymmetrization of 5-monosubstituted 1,3-dicarbonyl substrates with ortho-quinone methides gives rise to valuable tetrahydroxanthenes containing two distant stereocenters.

Original languageEnglish (US)
Pages (from-to)13258-13263
Number of pages6
JournalAngewandte Chemie - International Edition
Volume53
Issue number48
DOIs
StatePublished - Nov 24 2014

Keywords

  • Cyclization
  • Enantioselectivity
  • Heterocycles
  • Organocatalysis
  • Synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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