title: Asymmetric Organocatalytic Reductive Coupling Reactions between Benzylidene Pyruvates and Aldehydes.
abstract: 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.
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599, United States.
authors.forename: Matthew A
authors.initials: MA
authors.lastname: Horwitz
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599, United States.
authors.forename: Blane P
authors.initials: BP
authors.lastname: Zavesky
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599, United States.
authors.forename: Jesus I
authors.initials: JI
authors.lastname: Martinez-Alvarado
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599, United States.
authors.forename: Jeffrey S
authors.initials: JS
authors.lastname: Johnson
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001597:Benzylidene Compounds / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry*; D017905:Phosphites / Q000737:chemistry*; D011773:Pyruvates / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001597:Benzylidene Compounds; D063065:Organophosphonates; D017905:Phosphites; D011773:Pyruvates; C047356:dimethyl hydrogen phosphite