Notes

Zervas, L.; Zioudrou, C.; Schuler, Bruno O. G.; Warren, F. L.; Craw, D. A.; Rogers, J. L.; Prasad, Karesh; Raper, R.; Meek, Eric G.; Anderson, D.M.W.; Greenwood, C. T.; Edward, J. T.

doi:10.1039/jr9560000214

Cited by 10 publications

(1 citation statement)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1,5‐Anhydro‐2,3,4,6‐tetra‐ O ‐benzyl‐ D ‐glucitol (25) : A solution of 1‐bromo‐2,3,4,6‐tetra‐ O ‐acetyl‐α‐ D ‐glucose (1.8 g, 4.38 mmol) in Et 2 O (5 mL) was slowly added to a stirred suspension of LiAlH 4 (1.19 g, 45 mmol) in Et 2 O (27 mL) under argon at 0 °C. After 1 h at room temperature, the reaction mixture was hydrolysed carefully with water and then filtered through a celite pad 56. The aqueous layer was neutralised with IR120 H + , concentrated under vacuum and dried over P 2 O 5 .…”

Section: Methodsmentioning

confidence: 99%

Triisobutylaluminium and Diisobutylaluminium Hydride as Molecular Scalpels: The Regioselective Stripping of Perbenzylated Sugars and Cyclodextrins

Lecourt

Herault

Pearce

et al. 2004

Chemistry A European J

167

130

View full text Add to dashboard Cite

To explain the remarkable regioselective de-O-benzylating properties of diisobutylaluminium hydride (DIBAL-H) and triisobutylaluminium (TIBAL) towards polybenzylated sugars or cyclodextrins, we propose a plausible mechanistic rationale critically involving the kinetic formation of a product-generating 2:1 Al-benzylated sugar complex. For the reaction to occur, one pair of adjacent oxygen atoms should first be able to form a chelation complex with the first equivalent of aluminium reagent, either a highly fluxional complex with tetracoordinate aluminium species or a pentacoordinate one. The second equivalent then induces the regioselectivity of the de-O-alkylation by coordinating preferentially to one of the oxygen atoms of the selected pair.

show abstract

Section: Methodsmentioning

confidence: 99%