Diastereo- and Enantioselective Construction of a Bispirooxindole Scaffold Containing a Tetrahydro-β-carboline Moiety through an Organocatalytic Asymmetric Cascade Reaction

• Published in: Chemistry : a European journal Vol. 20; no. 36; pp. 11382 - 11389
• Main Authors: Dai, Wei, Lu, Han, Li, Xin, Shi, Feng, Tu, Shu-Jiang
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.09.2014; WILEY‐VCH Verlag; Wiley
• Subjects: asymmetric synthesis; Asymmetry; bispirooxindoles; Carbolines - chemistry; Cascade chemical reactions; Cascades; Catalysis; Catalysts; Chemistry; Chemistry, Multidisciplinary; Construction; enantioselectivity; Indoles - chemical synthesis; Indoles - chemistry; Models, Molecular; multicomponent reactions; organocatalysis; Phosphoric Acids - chemistry; Physical Sciences; Scaffolds; Science & Technology; Spiro Compounds - chemical synthesis; Spiro Compounds - chemistry; Stereoisomerism; Stereoselectivity; enantioselectivity; multicomponent reactions; 1,3-DIPOLAR CYCLOADDITIONS; DIELS-ALDER REACTIONS; OXINDOLES; PICTET-SPENGLER REACTIONS; CONTIGUOUS STEREOCENTERS; HIGHLY EFFICIENT; organocatalysis; asymmetric synthesis; PHOSPHORIC-ACID; bispirooxindoles; CHIRAL BRONSTED ACID; SPIROCYCLOPENTANE BIOXINDOLES; DERIVATIVES

The first catalytic asymmetric construction of a new class of bispirooxindole scaffold‐containing tetrahydro‐β‐carboline moiety has been established through chiral phosphoric acid‐catalyzed three‐component cascade Michael/Pictet–Spengler reactions of isatin‐derived 3‐indolylmethanols, isatins, and a...