Organocatalytic Asymmetric Formal [4 + 2] Cycloaddition of in Situ Oxidation-Generated ortho-Quinone Methides and Aldehydes

Ding Zhou, Xueting Yu, Jian Zhang, Wei Wang, Hexin Xie

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

An unprecedented chiral secondary amine-catalyzed formal [4 + 2] annulation of aldehydes and oxidation-generated β-unsubstituted o-QMs is reported. This asymmetric protocol allows direct functionalization of the benzylic C-H bonds and furnishes [4 + 2] cycloadducts, chromanols, with excellent enantioselectivity and in up to 92% yield. The usability of this approach was further demonstrated by the enantioselective synthesis of anticancer Rhinacanthins derivative NKPLS8.

Original languageEnglish (US)
Pages (from-to)174-177
Number of pages4
JournalOrganic Letters
Volume20
Issue number1
DOIs
StatePublished - Jan 5 2018
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Organocatalytic Asymmetric Formal [4 + 2] Cycloaddition of in Situ Oxidation-Generated ortho-Quinone Methides and Aldehydes'. Together they form a unique fingerprint.

Cite this