<b>Mechanism of Thiamine Action: a Model of 2-Acylthiamine</b>

White, Fred G.; Ingraham, Lloyd L.

doi:10.1021/ja00875a015

Cited by 48 publications

(12 citation statements)

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“…Here, the thiamine analog, as a good leaving group, behaves as a "highenergy" acylating agent (608). A similar role is postulated for the pyrimidine ring of thiamine.…”

Section: T T Ho Tmentioning

confidence: 87%

Bioorganic Chemistry

Dugas¹

1989

Springer Advanced Texts in Chemistry

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“…Here, the thiamine analog, as a good leaving group, behaves as a "highenergy" acylating agent (608). A similar role is postulated for the pyrimidine ring of thiamine.…”

Section: T T Ho Tmentioning

confidence: 87%

Bioorganic Chemistry

Dugas¹

1989

Springer Advanced Texts in Chemistry

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“…Another interesting model is the following: Here, the thiamine analogue, as a good leaving group, behaves as a "high energy" acylating agent (327).…”

Section: O IImentioning

confidence: 99%

Bioorganic Chemistry

Dugas

Penney

1981

Springer Advanced Texts in Chemistry

110

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“…Previous work inspired by interest in thiamine catalysis led to the study of stoichometrically generated acyl azoliums derived from imidazolylidene and thiazolylidene carbenes and their capacity to react with nucleophiles. Contributions from Breslow, [16b] Daigo, [39] White and Ingharam, [40] Bruice, [41] Lienhard and Owen [42] revealed that water was the most proficient nucleophile followed by alcohols and amines. Additionally, work by Bode has recently confirmed this paradox of nucleophilicity versus reactivity with triazolylidene derived acyl azoliums.…”

Section: Nhc Redox Acylationmentioning

confidence: 99%

Exploiting Acyl and Enol Azolium Intermediates via N‐Hetero‐ cyclic Carbene‐Catalyzed Reactions of α‐Reducible Aldehydes

2012

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N-heterocyclic carbenes are well known for their role in catalyzing benzoin and Stetter reactions: the generation of acyl anion equivalents from simple aldehydes to react with a variety of electrophiles. However, when an aldehyde bearing a leaving group or unsaturation adjacent to the acyl anion equivalent is subjected to an NHC, a new avenue of reactivity is unlocked, leading to a number of novel transformations which can generate highly complex products from simple starting materials, many of which are assembled through unconventional bond disconnections. The field of these new reactions - those utilizing α-reducible aldehydes to access previously unexplored catalytic intermediates – has expanded rapidly in the past eight years. This review aims to provide the reader with a historical perspective on the underlying discoveries that led to the current state of the art, a mechanistic description of these reactions, and a summary of the recent advances in this area.

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Mechanism of Thiamine Action: a Model of 2-Acylthiamine

Cited by 48 publications

References 1 publication

Bioorganic Chemistry

Bioorganic Chemistry

Bioorganic Chemistry

Exploiting Acyl and Enol Azolium Intermediates via N‐Hetero‐ cyclic Carbene‐Catalyzed Reactions of α‐Reducible Aldehydes

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