Coenzyme-inspired chemistry 2: 4,5-dihydroimidazolium ylides (NHCs) and the reactions of 2-(1-hydroxyalkyl)-4,5-dihydroimidazoles

Ketones are prepared from aldehydes via 1-benzyl-2-(1-hydroxyalkyl)-4,5-dihydroimidazoles (adducts of the aldehydes with 1-benzyl-2-lithio-4,5-dihydroimidazoles) whereas 1-benzyl-2-(1-oxoalkyl)-4,5-dihydroimidazoles are shown to act as acyl transfer reagents via C-C bond cleavage. 4,5-Dihydroimidazo...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2013-09, Vol.11 (35), p.5926-5935
Main Authors: Jones, Raymond C. F, Nichols, John R
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Imidazoles - chemical synthesis
Imidazoles - chemistry
Ketones - chemistry
Stereoisomerism
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Summary:Ketones are prepared from aldehydes via 1-benzyl-2-(1-hydroxyalkyl)-4,5-dihydroimidazoles (adducts of the aldehydes with 1-benzyl-2-lithio-4,5-dihydroimidazoles) whereas 1-benzyl-2-(1-oxoalkyl)-4,5-dihydroimidazoles are shown to act as acyl transfer reagents via C-C bond cleavage. 4,5-Dihydroimidazolium ylides (NHCs) are intermediates in both processes, which constitute thiamine-inspired C-C bond formation and cleavage protocols. Adducts of 2-lithio-4,5-dihydroimidazoles with carbonyl compounds fragment by loss of an NHC in C-C bond formation/cleavage processes inspired by thiamine.
ISSN:1477-0520
1477-0539
DOI:10.1039/c3ob40884a