title: Organocatalytic domino Michael-Knoevenagel condensation reaction for the synthesis of optically active 3-diethoxyphosphoryl-2-oxocyclohex-3-enecarboxylates.
abstract: Versatile dominoes: A novel, organocatalytic, Michael-Knoevenagel condensation domino reaction of ethyl 4-diethoxyphosphoryl-3-oxobutanoate with various aryl- and aliphatic-substituted alpha,beta-unsaturated aldehydes catalyzed by a chiral diarylprolinol ether has been successfully performed. The reaction proceeds in a highly enantio- and diastereoselective manner giving access to optically active 6-substituted-3-diethoxyphosphoryl-2-oxocyclohex-3-enecarboxylates (see scheme).A novel, organocatalytic, highly enantio- and diastereoselective synthetic approach towards optically active 6-substituted-3-diethoxyphosphoryl-2-oxocyclohex-3-enecarboxylates is presented. Our methodology utilizes a Michael-Knoevenagel domino reaction sequence of ethyl 4-diethoxyphosphoryl-3-oxobutanoate and alpha,beta-unsaturated aldehydes catalyzed by a chiral diarylprolinol ether. The cyclohexenecarboxylates obtained are particularly well suited for the preparation of highly functionalized cyclohexene and cyclohexane derivatives, with up to four chiral centers and high levels of stereocontrol.
authors.affiliation: Department of Chemistry, Danish National Research Foundation: Centre for Catalysis, Aarhus University 8000 Aarhus C, Denmark.
authors.forename: Łukasz
authors.initials: Ł
authors.lastname: Albrecht
authors.forename: Bo
authors.initials: B
authors.lastname: Richter
authors.forename: Carlos
authors.initials: C
authors.lastname: Vila
authors.forename: Henryk
authors.initials: H
authors.lastname: Krawczyk
authors.forename: Karl Anker
authors.initials: KA
authors.lastname: Jørgensen
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D053138:Cyclohexenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D002264:Carboxylic Acids; D053138:Cyclohexenes; D009943:Organophosphorus Compounds; C052568:cyclohexene