Stereocontrol in the intramolecular Buchner reaction of diazoamides and diazoesters

C J Moody, S Miah, A M Z Slawin, D J Mansfield, I C Richards

Research output: Contribution to journalArticlepeer-review

28 Citations (Scopus)

Abstract

Dirhodium(II) catalysed decomposition of diazoamide 5 resulted in formation of beta-lactams 6/7 by intramolecular C-H insertion, the intramolecular Buchner reaction being disfavoured for conformational reasons. The diazoamide 8, however gave products resulting from both the intramolecular Buchner reaction and C-H insertion. Chiral diazoesters 14-16 derived from a-substituted benzyl alcohols gave cycloheptatrienes in a highly diastereoselective manner; the norcaradiene isomer of the cycloheptatrienes was readily intercepted in a Diels-Alder reaction with 4-phenyl-1,2,4-triazoline-3.5-dione to give adducts 19-21.

Original languageEnglish
Pages (from-to)4067-4075
Number of pages9
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number24
Publication statusPublished - 21 Dec 1998

Keywords

  • C-H INSERTION
  • ARYL DIAZOKETONES
  • CATALYTIC DECOMPOSITION
  • CYCLOADDITIONS
  • CONSTRUCTION
  • CARBENOIDS
  • LACTONES
  • ESTERS

Fingerprint

Dive into the research topics of 'Stereocontrol in the intramolecular Buchner reaction of diazoamides and diazoesters'. Together they form a unique fingerprint.

Cite this