Asymmetric Michael addition of gamma,gamma-disubstituted alpha,beta-unsaturated aldehydes to nitroolefins via dienamine catalysis.
The first chemo- and alpha-regioselective asymmetric Michael addition of gamma,gamma-disubstituted alpha,beta-unsaturated aldehydes to nitroolefins has been presented in excellent diastereo- and enantioselectivities (dr up to >99:1, 93-96% ee) via dienamine catalysis. The Michael adducts have been efficiently converted to a number of optically pure cyclic frameworks with versatile scaffold diversity.
Han
Bo
B
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.
Xiao
You-Cai
YC
He
Zhao-Quan
ZQ
Chen
Ying-Chun
YC
D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D013237:Stereoisomerism; D013379:Substrate Specificity
D000447:Aldehydes; D000475:Alkenes; D000588:Amines