Catalytic Divergent [3+3]- and [3+2]-Cycloaddition by Discrimination Between Diazo Compounds

Yongming Deng, Lynée A. Massey, Yeray A. Rodriguez Núñez, Hadi Arman, Michael P. Doyle

Research output: Contribution to journalArticlepeer-review

37 Citations (Scopus)

Abstract

Highly selective divergent cycloaddition reactions of enoldiazo compounds and α-diazocarboximides catalyzed by copper(I) or dirhodium(II) have been developed. With tetrakis(acetonitrile)copper(I) tetrafluoroborate as the catalyst epoxypyrrolo[1,2-a]azepine derivatives were prepared in good yields and excellent diastereoselectivities through the first reported [3+3]-cycloaddition of a carbonyl ylide. Use of Rh2(pfb)4 or Rh2(esp)2 directs the reactants to regioselective [3+2]-cycloaddition generating cyclopenta[2,3]pyrrolo[2,1-b]oxazoles with good yields and excellent diastereoselectivities.

Original languageEnglish
Pages (from-to)12292-12296
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number40
DOIs
Publication statusPublished - 2017
Externally publishedYes

Keywords

  • copper
  • cycloaddition
  • diazo compounds
  • rhodium
  • ylides

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint

Dive into the research topics of 'Catalytic Divergent [3+3]- and [3+2]-Cycloaddition by Discrimination Between Diazo Compounds'. Together they form a unique fingerprint.

Cite this