Carbanion-accelerated Claisen rearrangements 5. Studies on stereocontrol with phosphorus-stabilized anions

Scott E. Denmark, G. Rajendra, John E. Marlin

Research output: Contribution to journalArticle


The allyl vinyl ethers 1 undergo facile and highly diastereoselective carbanionic Claisen rearrangements. The selectivity of the reaction depends on the counterion and the size of the group on the 1,3,2-oxazaphosphorinane nitrogen atom. The origin of the high selectivity is discussed.

Original languageEnglish (US)
Pages (from-to)2469-2472
Number of pages4
JournalTetrahedron Letters
Issue number19
StatePublished - 1989


ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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