title: One-pot enantioselective construction of indoloquinolizidine derivatives bearing five contiguous stereocenters using aliphatic aldehydes, nitroethylenes, and tryptamine.
abstract: An organocatalytic cascade reaction was established for the construction of indoloquinolizidine derivatives bearing five contiguous stereocenters from readily available aliphatic aldehydes, nitroethylenes, and tryptamine. This one-pot process gave 30-55% overall yields with excellent d.r. (>20 : 1 in all cases) and ee (91-98%). Additionally, quaternary stereogenic carbon center-containing indoloquinolizidines were prepared through NBS-mediated cyclization of one of the intermediates.
authors.affiliation: Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China. sunxingwen@fudan.edu.cn lingq@sioc.ac.cn.
authors.forename: Yu
authors.initials: Y
authors.lastname: Tan
authors.forename: Han-Lin
authors.initials: HL
authors.lastname: Luan
authors.forename: Hua
authors.initials: H
authors.lastname: Lin
authors.forename: Xing-Wen
authors.initials: XW
authors.lastname: Sun
authors.forename: Xiao-Di
authors.initials: XD
authors.lastname: Yang
authors.forename: Han-Qing
authors.initials: HQ
authors.lastname: Dong
authors.forename: Guo-Qiang
authors.initials: GQ
authors.lastname: Lin
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic / Q000379:methods; D005030:Ethylenes / Q000737:chemistry*; D045563:Indolequinones / Q000138:chemical synthesis*; D054837:Quinolizidines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014363:Tryptamines / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D005030:Ethylenes; D045563:Indolequinones; D054837:Quinolizidines; D014363:Tryptamines; C030820:tryptamine