Highly Enantio- and Diastereoselective [4 + 2] Cycloaddition of 5H-oxazol-4-ones with N-Maleimides

Shuai Qiu, Richmond Lee, Bo Zhu, Michelle L. Coote, Xiaowei Zhao, Zhiyong Jiang

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

An organocatalytic asymmetric reaction between 5H-oxazol-4-ones and N-substituted maleimides is disclosed. Employing Takemoto's chiral tertiary amine-thiourea as the catalyst, [4 + 2] annulation reactions were performed with high chemoselectivity, leading to a series of biologically important chiral oxo-bridged piperidone-fused succinimides in good to excellent enantioselectivities (up to >99% ee) and >19:1 dr.

Original languageEnglish
Pages (from-to)8061-8069
Number of pages9
JournalJournal of Organic Chemistry
Volume81
Issue number17
DOIs
Publication statusPublished - 2 Sep 2016
Externally publishedYes

Bibliographical note

Funding Information:
We are grateful for the grants from NSFC (21072044) and Henan province (14IRTSTHN006, 152300410057, 162300410002).

Publisher Copyright:
© 2016 American Chemical Society.

Keywords

  • Enantio
  • Diastereoselective
  • Cycloaddition
  • N-Maleimides
  • allylic
  • alkylation
  • chiral
  • molecules

Fingerprint

Dive into the research topics of 'Highly Enantio- and Diastereoselective [4 + 2] Cycloaddition of 5H-oxazol-4-ones with N-Maleimides'. Together they form a unique fingerprint.

Cite this