Intramolecular anodic olefin coupling reactions: Use of the reaction rate to control substrate/product selectivity

Hai Chao Xu, Kevin D. Moeller

Research output: Contribution to journalArticlepeer-review

62 Scopus citations

Abstract

Look out-it's a trap! The anodic coupling of olefins with amine trapping groups to form proline and pipecolic acid derivatives with a quaternary α carbon atom (see scheme) was successful despite the significantly lower oxidation potential of the product relative to that of either functional group in the substrate: owing to the very fast cyclization, the oxidation potential of the substrate is lower than that of the product. Ts=p-toluenesulfonyl.

Original languageEnglish
Pages (from-to)8004-8007
Number of pages4
JournalAngewandte Chemie - International Edition
Volume49
Issue number43
DOIs
StatePublished - Oct 18 2010

Keywords

  • Amino acids
  • Cyclization
  • Dithioketene acetals
  • Electrochemistry
  • Oxidation potential

Fingerprint

Dive into the research topics of 'Intramolecular anodic olefin coupling reactions: Use of the reaction rate to control substrate/product selectivity'. Together they form a unique fingerprint.

Cite this