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 | Zendy

Kirschning Andreas | Zendy

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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

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.

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