Development of a Phase-Transfer-Catalyzed, [2,3]-Wittig Rearrangement

Scott E Denmark, Lindsey R. Cullen

Research output: Contribution to journalArticle

Abstract

An investigation into the use of phase-transfer catalysis for the [2,3]-sigmatropic rearrangement of allyloxy carbonyl compounds is described. Initial studies focused on identifying viable substrate classes that would undergo selective [2,3]-rearrangement under phase-transfer catalysis. Under certain conditions, the [2,3]-sigmatropic rearrangement of allyloxy carbonyl compounds takes place in the presence of a phase-transfer agent, providing a rare example of a phase-transfer-catalyzed unimolecular reaction. In the course of this investigation, it was found that catalysis is dependent on several variables including base concentration, catalyst structure, and substrate lipophilicity. Preliminary testing of chiral, nonracemic phase-transfer catalysts has shown promising levels of enantioselectivity for future development.

Original languageEnglish (US)
Pages (from-to)11818-11848
Number of pages31
JournalJournal of Organic Chemistry
Volume80
Issue number23
DOIs
StatePublished - Oct 2 2015

ASJC Scopus subject areas

  • Organic Chemistry

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