title: Synthesis of six-membered spirocyclic oxindoles with five consecutive stereocenters in an asymmetric organocatalytic one-pot Michael/Michael/aldol addition sequence.
abstract: An asymmetric organocatalytic one-pot synthesis of six-membered spirocyclic oxindoles has been successfully developed through a relay Michael/Michael/aldol addition reaction catalyzed by the combination of readily available diphenylprolinol silyl ether and bifunctional quinine thiourea. The one-pot protocol affords the highly substituted spirocyclic oxindoles in high yields and perfect enantioselectivities. More importantly, through judicious choice of the organocatalysts employed, this reaction could be readily adapted to predominantly afford an alternative major diastereomer of the product.
authors.affiliation: Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Road Zu Chong Zhi, Zhangjiang Hi-Tech Park, Shanghai 201203, People's Republic of China. zhoubing2012@hotmail.com
authors.forename: Bing
authors.initials: B
authors.lastname: Zhou
authors.forename: Yaxi
authors.initials: Y
authors.lastname: Yang
authors.forename: Jingjing
authors.initials: J
authors.lastname: Shi
authors.forename: Zhi
authors.initials: Z
authors.lastname: Luo
authors.forename: Yuanchao
authors.initials: Y
authors.lastname: Li
mesh_terms: D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009930:Organic Chemicals / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007211:Indoles; D009930:Organic Chemicals; D013141:Spiro Compounds