Journal
ORGANIC LETTERS
Volume 12, Issue 1, Pages 52-55Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol902459z
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Funding
- National Institute of General Medical Sciences [GM-65597]
- National Cancer Institute of the United States National Institutes of Health [CA-76497]
- NATIONAL CANCER INSTITUTE [R01CA076497] Funding Source: NIH RePORTER
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM065597] Funding Source: NIH RePORTER
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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.
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