1202810-35-2Relevant academic research and scientific papers
Dynamic kinetic resolution during a vinylogous Payne rearrangement: A concise synthesis of the polar pharmacophoric subunit of (+)-scyphostatin
Hoye, Thomas R.,Jeffrey, Christopher S.,Nelson, Dorian P.
, p. 52 - 55 (2010)
"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.
