Tetrahedron Chem | |
Organocatalytic asymmetric synthesis of bioactive hexahydropyrrolo[2,3-b]indole-containing tetrasubstituted allenes bearing multiple chiral elements | |
Wei Tan1  Shuming Zhang2  Shu Zhang2  Xian-Yang Yu3  Hong-Lin Wan3  Jing-Yi Wang3  Yu-Hao Wang3  Feng Shi3  | |
[1] Corresponding author.;Department of Gerontology, Department of Radiotherapy, The First Affiliated Hospital of Nanjing Medical University, Nanjing, 210029, China;School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, 221116, China; | |
关键词: Asymmetric organocatalysis; Axial chirality; Catalytic asymmetric dearomatization; para-quinone methides; Chiral phosphoric acid; | |
DOI : | |
来源: DOAJ |
【 摘 要 】
An organocatalytic asymmetric construction of hexahydropyrrolo[2,3-b]indole-containing tetrasubstituted allene scaffolds bearing both axial chirality and central chirality has been established via a cascade 1,8-addition/dearomatization-cyclization reaction of para-aminophenyl propargylic alcohols with tryptamines in the presence of chiral phosphoric acid (CPA), thus affording a wide range of such tetrasubstituted allenes bearing multiple chiral elements in generally good yields (up to 94%) with high diastereo- and enantioselectivities (up to 95:5 dr, 95% ee). In addition, the evaluation on the cytotoxicity of some selected products indicated that this class of chiral tetrasubstituted allenes could inhibit the growth of the pancreatic cancer cells to some extent. This work not only solved the challenging issues in enantioselective construction of tetrasubstituted allenes via alkynyl (aza)-para-quinone methides, but also represents the first example of using alkyne derivatives as electrophiles in organocatalytic asymmetric dearomatizations of tryptamines.
【 授权许可】
Unknown