title: Asymmetric tandem Michael addition-Wittig reaction to cyclohexenone annulation.
abstract: A highly stereoselective tandem Michael addition-Wittig reaction of (3-carboxy-2-oxopropylidene)triphenylphosphorane and alpha,beta-unsaturated aldehydes has been developed by employing the combined catalysis of a newly designed bulky chiral secondary amine 1g, LiClO(4), and DABCO. The multifunctional 6-carboxycyclohex-2-en-1-ones were generally obtained in excellent diastereo- and enantioselectivities (dr up to >50:1, 86-99% ee).
authors.affiliation: Key Laboratory of Drug-Targeting and Drug Delivery System of Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
authors.forename: Yan-kai
authors.initials: YK
authors.lastname: Liu
authors.forename: Chao
authors.initials: C
authors.lastname: Ma
authors.forename: Kun
authors.initials: K
authors.lastname: Jiang
authors.forename: Tian-Yu
authors.initials: TY
authors.lastname: Liu
authors.forename: Ying-Chun
authors.initials: YC
authors.lastname: Chen
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010753:Phosphoranes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C542076:(3-carboxy-2-oxopropylidene)triphenylphosphorane; D000447:Aldehydes; D000588:Amines; D003512:Cyclohexanones; D010753:Phosphoranes