2005
DOI: 10.1002/ejoc.200400584
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Reinvestigation of the Mechanism of gem‐Diacylation: Chemoselective Conversion of Aldehydes to Various gem‐Diacylates and Their Cleavage under Acidic and Basic Conditions

Abstract: The mechanism of gem-diacylate formation has been studied extensively using tetrabutylammonium tribromide (TBATB) as the catalyst. The reaction proceeds by a nucleophilic attack of an anhydride on an aldehydic carbonyl group, nucleophilic attack of the hemiacylate intermediate on a second molecule of the anhydride, followed by an intermolecular attack of a second acetate group to regenerate the anhydride. gem-Diacylates of various aliphatic and aromatic aldehydes were obtained directly from the reaction of a v… Show more

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Cited by 34 publications
(28 citation statements)
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References 79 publications
(67 reference statements)
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“…27 A wide variety of organic transformations have also been developed by others involving tetrabutylammonium tribromide (TBATB). [28][29][30][31][32][33] Knowing the unique behavior, properties, and stabilities of these reagents, we conceived the idea that tetrabutylammonium tribromide (TBATB) 0008-6215/$ -see front matter Ó 2011 Elsevier Ltd. All rights reserved. doi:10.1016/j.carres.2010.12.018 might be a useful catalyst for the preparation of various O-isopropylidene derivatives from sugars.…”
Section: Introductionmentioning
confidence: 99%
“…27 A wide variety of organic transformations have also been developed by others involving tetrabutylammonium tribromide (TBATB). [28][29][30][31][32][33] Knowing the unique behavior, properties, and stabilities of these reagents, we conceived the idea that tetrabutylammonium tribromide (TBATB) 0008-6215/$ -see front matter Ó 2011 Elsevier Ltd. All rights reserved. doi:10.1016/j.carres.2010.12.018 might be a useful catalyst for the preparation of various O-isopropylidene derivatives from sugars.…”
Section: Introductionmentioning
confidence: 99%
“…[9], LiBF 4 [10], NBS [11], I 2 [12], TMSCl-NaI [13], FeCl 3 [14], CoCl 2 [17] and tetrabutylammonium tribromide (TBATB) [18]. Some metal triflates, e.g.…”
Section: Introductionmentioning
confidence: 99%
“…de R 3 = Ph and Me) and, when the reactions are carried out in THF, they show some diastereoselectivity. The rearrangement of 5-hydroxycycloctanone (3) to its hemiacetal (4) has been studied computationally. 2 A concerted intramolecular nucleophilic addition process is demonstrated.…”
Section: Formation and Reactions Of Acetals And Related Speciesmentioning
confidence: 99%
“…4 Deprotection can be achieved with the same catalyst on addition of methanol. The reaction proceeds via protonation of aldehyde, nucleophilic attack of the anhydride, and further nucleophilic attack on the hemiacylate intermediate, followed by regeneration of anhydride.…”
Section: Formation and Reactions Of Acetals And Related Speciesmentioning
confidence: 99%
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