Catalytic asymmetric β,γ activation of α,β-unsaturated γ-butyrolactams: direct approach to β,γ-functionalized dihydropyranopyrrolidin-2-ones.
Skeleton in the closet: The title reaction enables the development of the first catalytic β,γ-selective Diels-Alder [4+2] annulation of α,β-unsaturated γ-butyrolactams (see scheme; Boc=tert-butoxycarbonyl, Ts=4-toluenesulfonyl). This process provides a direct method for the enantioselective construction of bi- or tricyclic dihydropyranopyrrolidin-2-one skeletons in only one step.
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Institute of Biochemistry and Molecular Biology, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000 (China). wangrui@lzu.edu.cn.
Xianxing
X
Jiang
Luping
L
Liu
Panpan
P
Zhang
Yuan
Y
Zhong
Rui
R
Wang
D002384:Catalysis; D061565:Cycloaddition Reaction; D006571:Heterocyclic Compounds; D007769:Lactams / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D006571:Heterocyclic Compounds; D007769:Lactams
annulation; asymmetric catalysis; cycloadditions; heterocycles; synthetic methods