Dynamic kinetic resolution during a vinylogous Payne rearrangement: A concise synthesis of the polar pharmacophoric subunit of (+)-scyphostatin

Thomas R. Hoye, Christopher S. Jeffrey, Dorian P. Nelson

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

"Chemical Equation Presented" The diastereomeric epoxycyclohexenols 3a/b (obtained via a Wharton rearrangement of a bis-epoxycyclohexanone precursor) were shown to undergo interconversion via a facile vinylogous Payne rearrangement. Mechanistic issues were probed; the doubly O-deuterated analogues underwent this equilibration more slowly than the parent dihydroxy compounds. It was possible to kinetically resolve the mixture of 3a/b under equilibrating conditions by use of Amano PS. This DKR is additionally noteworthy because it sets four stereocenters in a single event.

Original languageEnglish (US)
Pages (from-to)52-55
Number of pages4
JournalOrganic Letters
Volume12
Issue number1
DOIs
StatePublished - Jan 1 2010

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