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3,4‐bis( O‐tert ‐butyldimethylsilyl)‐6‐ O ‐tosyl‐ D ‐glucal: A probe for the mechanism of the iodine(III)‐promoted allylic oxidation of glycals
Author(s) -
Kirschning Andreas
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199511289
Subject(s) - glucal , chemistry , allylic rearrangement , tosyl , reagent , stereoselectivity , hypervalent molecule , iodine , enol , medicinal chemistry , organic chemistry , catalysis
Abstract The reaction of 3,4‐bis( O ‐ tert ‐butyldimethylsilyl)‐6‐ O ‐tosyl‐ D ‐glucal 4 with the Koser reagent [PhI(OH)OTs] unexpectedly afforded tetrahydrofurfural 6 as well as 2,3‐anhydropyranose 7 as major products. This unprecedented, stereoselective transformation helps to gain further insight into the mechanism of the well‐documented hypervalent iodine‐promoted allylic oxidation of cyclic enol ethers. A novel chemoenzymatic method for the preparation of glucal 4 in high yield is presented.