Diphenylprolinol silyl ether catalysis in an asymmetric formal carbo [3 + 3] cycloaddition reaction via a domino Michael/Knoevenagel condensation.
Diphenylprolinol silyl ether was found to catalyze the formal carbo [3 + 3] cycloaddition reaction through the domino reaction via the Michael reaction, followed by Knoevenagel condensation of the alpha,beta-unsaturated aldehyde and dimethyl 3-oxopentanedioate, affording substituted cyclohexenone derivatives with excellent enantioselectivity.
Hayashi
Yujiro
Y
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan. hayashi@ci.kagu.tus.ac.jp
Toyoshima
Maya
M
Gotoh
Hiroaki
H
Ishikawa
Hayato
H
D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D053138:Cyclohexenes / Q000138:chemical synthesis* / Q000737:chemistry; D004987:Ethers / Q000737:chemistry*; D007656:Ketoglutaric Acids / Q000737:chemistry; D015394:Molecular Structure; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D053138:Cyclohexenes; D004987:Ethers; D007656:Ketoglutaric Acids; C524329:dimethyl 1,3-acetonedicarboxylate; C529940:diphenylprolinol silyl ether; D011392:Proline