Organocatalytic domino Michael-Knoevenagel condensation reaction for the synthesis of optically active 3-diethoxyphosphoryl-2-oxocyclohex-3-enecarboxylates.
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.
Albrecht
Łukasz
Ł
Department of Chemistry, Danish National Research Foundation: Centre for Catalysis, Aarhus University 8000 Aarhus C, Denmark.
Richter
Bo
B
Vila
Carlos
C
Krawczyk
Henryk
H
Jørgensen
Karl Anker
KA
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
D000447:Aldehydes; D002264:Carboxylic Acids; D053138:Cyclohexenes; D009943:Organophosphorus Compounds; C052568:cyclohexene