Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 17, Issue 7, Pages 1901-1905Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8ob02141d
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Funding
- 1000-Youth Talents Plan start-up funding
- National Natural Science Foundation of China [21772183]
- University of Science and Technology of China
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In this protocol we described a boronic acid-catalysed C-3 selective ring opening of 3,4-epoxy alcohols with thiophenols and thiols as nucleophiles. This diastereo-and enantiospecific reaction provides an efficient entry to prepare a variety of hydroxyl sulfides. Through the directing effect of the hydroxyl group, nucleophilic attack on the C-3 position of the epoxide moiety is favoured. It can be rationalized in a proposed transition state, in which the boronic acid catalyst tethers both epoxides and S-nucleophiles.
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