Intercepting the Nazarov Oxyallyl Intermediate with α-Formyl-vinyl Anion Equivalents to Access Formal Morita-Baylis-Hillman Alkylation Products

Yen Ku Wu, Rongrong Lin, F. G. West

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

A Lewis acid catalyzed cationic domino reaction involving sequential electrocyclization and polar addition of allenol ethers onto the resulting oxyallyl species is described. The overall sequence allows a highly stereoselective synthesis of densely substituted cyclopentanoid compounds containing α-formylvinyl functionality which is formally equivalent to products of a Morita-Baylis-Hillman alkylation process.

Original languageEnglish (US)
Article numberst-2017-r0080-l
Pages (from-to)1486-1490
Number of pages5
JournalSynlett
Volume28
Issue number12
DOIs
StatePublished - Jul 24 2017

Keywords

  • Morita-Baylis-Hillman alkylation
  • allenol ethers
  • carbonyl umpolung
  • interrupted Nazarov cyclization
  • oxyallyl cation

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