A highly efficient asymmetric synthesis of quaternary stereocenter-containing indolizidine and quinolizidine alkaloids using aldehydes, nitroalkenes, and unactivated cyclic ketimines.
A highly efficient approach for the construction of indolizidines and quinolizidines bearing a bridged quaternary stereocenter has been established in a one-pot fashion using aldehydes, nitroalkenes, and cyclic ketimines with excellent enantioselectivities and in high yields. Moreover, this method could be applied to the synthesis of indolizidines in the gram scale.
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China. sunxingwen@fudan.edu.cn lingq@sioc.ac.cn.
Yu
Y
Tan
Yong-Jian
YJ
Chen
Hua
H
Lin
Han-Lin
HL
Luan
Xing-Wen
XW
Sun
Xiao-Di
XD
Yang
Guo-Qiang
GQ
Lin
D000447:Aldehydes / Q000737:chemistry*; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D007097:Imines / Q000737:chemistry*; D054836:Indolizidines / Q000737:chemistry*; D008968:Molecular Conformation; D009570:Nitriles / Q000737:chemistry*; D054837:Quinolizidines / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D000470:Alkaloids; D000475:Alkenes; D007097:Imines; D054836:Indolizidines; D009570:Nitriles; D054837:Quinolizidines; C542835:ketimine