A flexible enantioselective approach to 2, 5-disubstituted cis-decahydroquinolines. (10th September 2022)

• Record Type: Journal Article
• Authors: Lang, Qi-Wei; Qian, Xiang-Yang; He, Xiu-Lin; Geng, Hui; Zheng, Jian-Feng; Huang, Pei-Qiang
• Is Part Of: Tetrahedron. Volume 122(2022)
• Publication Date: 2022-09-10
• Subjects: Decahydroquinolines -- Asymmetric synthesis -- Organocatalytic domino reaction -- Amide activation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2022.132935
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A flexible asymmetric approach to 2, 5-disubstituted cis -decahydroquinolines (DHQs) ring system from glutaraldehyde and methyl ( E )-5-nitropent-4-enoate is reported. The enantioselective organocatalytic domino Michael/Henry reaction, subsequent one-pot, four-step transformation involving desulfurization, concomitant nitro and alkene reduction and cyclization, and the one-pot amide reductive alkylation method are the key steps responsible for the stereoselective syntheses of 2, 5 - di -epi-cis -195 A, N -Bn-5- epi-cis -275 B' and N -Bn- cis -249D. Graphical abstract: Image 1