Breslow intermediate in organocatalysis

E601249

The Breslow intermediate in organocatalysis is a transient nucleophilic carbene-derived species central to thiamine- and N-heterocyclic carbene-catalyzed umpolung reactions of carbonyl compounds.

All labels observed (1)

Label Occurrences
Breslow intermediate in organocatalysis canonical 1

How this entity was disambiguated

Statements (46)

Predicate Object
instanceOf carbene-derived species ⓘ
nucleophilic carbene intermediate ⓘ
reaction intermediate ⓘ
enables nucleophilic reactivity at the former carbonyl carbon ⓘ
hasBeen characterized by spectroscopic methods in some systems ⓘ
hasChemicalNature carbene-derived ⓘ
nucleophilic ⓘ
hasElectronicCharacter acyl anion equivalent ⓘ
enaminol-like ⓘ
zwitterionic ⓘ
hasFunctionalGroupFeatures alpha-hydroxyalkyl substituent on carbene center ⓘ
conjugated C=C–O system ⓘ
hasPrecursor N-heterocyclic carbene catalyst ⓘ
aldehyde substrate ⓘ
carbonyl compound ⓘ
thiamine-derived carbene ⓘ
hasRole key intermediate in organocatalysis ⓘ
umpolung reagent ⓘ
hasStability short-lived ⓘ
isAssociatedWith biomimetic NHC catalysis ⓘ
thiamine pyrophosphate catalysis ⓘ
isCentralTo N-heterocyclic carbene-catalyzed umpolung reactions ⓘ
thiamine-catalyzed umpolung reactions ⓘ
isDerivedFrom N-heterocyclic carbene ⓘ
thiazolium carbene ⓘ
isDifficultTo isolate ⓘ
isDiscussedIn organocatalysis literature ⓘ
physical organic chemistry of carbenes ⓘ
isFormedBy addition of carbene to carbonyl carbon ⓘ
proton transfer from carbonyl carbon to carbene center ⓘ
isImportantFor design of NHC catalysts ⓘ
understanding thiamine-dependent enzymatic mechanisms ⓘ
isKeyTo reversal of polarity at the carbonyl carbon ⓘ
isNamedAfter Ronald Breslow ⓘ
isOften observed indirectly ⓘ
isTransient true ⓘ
isUsedIn organocatalytic C–C bond formation ⓘ
organocatalytic acylation reactions ⓘ
participatesIn NHC-catalyzed acyl anion equivalent chemistry ⓘ
Stetter reaction ⓘ
benzoin condensation ⓘ
umpolung of carbonyl compounds ⓘ
reactsWith Michael acceptors ⓘ
electrophilic carbonyl compounds ⓘ
wasProposedBy Ronald Breslow ⓘ
wasProposedIn 1958 ⓘ

How these facts were elicited

Referenced by (1)

Full triples — surface form annotated when it differs from this entity's canonical label.

Ronald Breslow → knownFor → Breslow intermediate in organocatalysis ⓘ