Construction of chiral bridged tricyclic benzopyrans: Enantioselective catalytic diels-alder reaction and a one-pot reduction/acid-catalyzed stereoselective cyclization

Aiguo Song, Xishuai Zhang, Xixi Song, Xiaobei Chen, Chenguang Yu, He Huang, Hao Li, Wei Wang

Research output: Contribution to journalArticlepeer-review

37 Scopus citations

Abstract

An asymmetric two-step approach to chiral bridged tricyclic benzopyrans, core structures featured in various natural products, is described. In the synthesis, an unprecedented enantioselective catalytic decarboxylative Diels-Alder reaction is developed using readily available coumarin-3-carboxylic acids and aldehydes as reactants under mild reaction conditions. Notably, the decarboxylation-assisted release of the catalyst enables the process to proceed efficiently with high enantio- and diastereoselectivity. Furthermore, a one-pot procedure for either a LiAlH4- or NaBH4-mediated reduction with subsequent acid-catalyzed intramolecular cyclization of the Diels-Alder adducts was identified for the efficient formation of the chiral bridged tricyclic benzopyrans.

Original languageEnglish (US)
Pages (from-to)4940-4944
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number19
DOIs
StatePublished - May 5 2014
Externally publishedYes

Keywords

  • cyclization
  • decarboxylation
  • heterocycles
  • organocatalysis
  • synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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