Diastereoselective syntheses of indoloquinolizidines by a Pictet-Spengler/lactamization cascade.
An expedient diastereoselective synthesis of highly functionalized indolo[2,3-α]quinolizidines adopting a cis H2/H12b geometry has been realized by a Pictet-Spengler/lactamization cascade sequence. The absolute stereochemistry at C2, C3, and C12b was governed by the originally created chirality of the Michael adduct through organocatalyzed conjugate addition of dialkyl malonates to α,β-unsaturated aldehydes.
Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, China.
Huihui
H
Fang
Xiaoyu
X
Wu
Linlin
L
Nie
Xiaoyang
X
Dai
Jie
J
Chen
Weiguo
W
Cao
Gang
G
Zhao
D018360:Crystallography, X-Ray; D007211:Indoles / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D054837:Quinolizidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D007211:Indoles; D007769:Lactams; D054837:Quinolizidines