Asymmetric tandem Michael addition-Wittig reaction to cyclohexenone annulation.
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).
Liu
Yan-kai
YK
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.
Ma
Chao
C
Jiang
Kun
K
Liu
Tian-Yu
TY
Chen
Ying-Chun
YC
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
C542076:(3-carboxy-2-oxopropylidene)triphenylphosphorane; D000447:Aldehydes; D000588:Amines; D003512:Cyclohexanones; D010753:Phosphoranes