Asymmetric Organocatalytic Reductive Coupling Reactions between Benzylidene Pyruvates and Aldehydes

Asymmetric Organocatalytic Reductive Coupling Reactions between Benzylidene Pyruvates and Aldehydes

An organocatalytic three-component reductive coupling reaction between dimethyl phosphite, benzylidene pyruvates, and aldehydes is reported. A chiral triaryl­iminophos­phorane catalyst promotes Pudovik addition, which is followed by phospha-Brook rearrangement to transiently generate enolates that a...

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Veröffentlicht in:Organic letters 2016-01, Vol.18 (1), p.36-39
Hauptverfasser: Horwitz, Matthew A, Zavesky, Blane P, Martinez-Alvarado, Jesus I, Johnson, Jeffrey S
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Benzylidene Compounds - chemistry
Catalysis
Molecular Structure
Organophosphonates - chemistry
Phosphites - chemistry
Pyruvates - chemistry
Stereoisomerism
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Zusammenfassung:An organocatalytic three-component reductive coupling reaction between dimethyl phosphite, benzylidene pyruvates, and aldehydes is reported. A chiral triaryl­iminophos­phorane catalyst promotes Pudovik addition, which is followed by phospha-Brook rearrangement to transiently generate enolates that are trapped stereoselectively by aldehydes. This reductive coupling provides vicinal polyfunctionalized stereocenters from readily available prochiral starting materials with excellent diastereoselectivity, enantioselectivity, and yield.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b03127