Journal
TETRAHEDRON LETTERS
Volume 45, Issue 7, Pages 1565-1566Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2003.11.084
Keywords
epoxides; nitric oxide; ring open
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Epoxide rings of 2,3-epoxy phenyl ketones were cleaved by nitric oxide, affording regioselectively the C-3 ring-opened products, erythro-alpha-hydroxyl nitrates (2), in a highly syn-selective mariner (isolated yield of the erythro products up to 91%). Products were identified by NMR, MS, and X-ray crystallography. The reaction is assumed to be initiated by NO2, unlike a nucleophilic attack. (C) 2003 Elsevier Ltd. All rights reserved.
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