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Stereoselective Synthesis of 3-Oxygenated- cis -dialkyl-2,5-substituted Tetrahydrofurans from Cyclohexadienediols

โœ Scribed by Brovetto, Margarita; Seoane, Gustavo


Book ID
120998915
Publisher
American Chemical Society
Year
2008
Tongue
English
Weight
433 KB
Volume
73
Category
Article
ISSN
0022-3263

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An expedient synthesis of 2,5-disubstitu
โœ Caroline L. Nesbitt; Christopher S.P. McErlean ๐Ÿ“‚ Article ๐Ÿ“… 2009 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 351 KB

Single enantiomer 2,5-disubstituted-3-oxygenated tetrahydrofurans are synthesized in as little as four steps from a commercially available epoxide. The key steps are homoallylic alcohol epoxidation, palladium-catalysed alkoxy-carbonylation-lactonisation and Mitsunobu inversion. The protocol is appli