A general asymmetric route to enantio-enriched isoflavanes via an organocatalytic annulation of o-quinone methides and aldehydes

Jian Zhang, Shuangzhan Zhang, Huixin Yang, Ding Zhou, Xueting Yu, Wei Wang, Hexin Xie

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

Reported herein is a general approach to optically active isoflavanes based on a chiral amine-catalyzed [4 + 2] asymmetric annulation of o-quinone methides and aldehydes. A number of naturally occurring isoflavanes, including equol, sativan, isosativan, vestitol and medicarpin, as well as isoflavane analogues were readily prepared with good to excellent enantioselectivities.

Original languageEnglish (US)
Pages (from-to)2407-2411
Number of pages5
JournalTetrahedron Letters
Volume59
Issue number25
DOIs
StatePublished - Jun 20 2018
Externally publishedYes

Keywords

  • Asymmetric
  • Isoflavanes
  • Organocatalysis
  • o-Quinone methide

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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