The first organocatalytic carbonyl-ene reaction: isomerisation-free C-C bond formations catalysed by H-bonding thio-ureas

Matthew L. Clarke, Charlotte E. S. Jones, Marcia B. France

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)

Abstract

Intramolecular carbonyl ene reactions of highly activated enophiles can be catalysed by H-bonding thio-ureas to give tertiary alcohols in high yields without extensive isomerisation side products. An asymmetric variant of this reaction was realised using a chiral thiourea but was limited by low enantioselectivity (up to 33% e. e.) and low turnover frequencies.

Original languageEnglish
Article number24
Number of pages4
JournalBeilstein Journal of Organic Chemistry
Volume3
DOIs
Publication statusPublished - 14 Sept 2007

Keywords

  • ASYMMETRIC CATALYSIS
  • COMPLEXES
  • ACIDS

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