Asymmetric aza-Friedel–Crafts reaction of indoles induced by O-pivaloylated d-galactosylamine as the chiral auxiliary

• Published in: Tetrahedron Vol. 68; no. 24; pp. 4830 - 4837
• Main Authors: Yang, Haohao, Cui, Bing, Wu, Guiping, Miao, Zhiwei, Chen, Ruyu
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 17.06.2012; Elsevier
• Subjects: Asymmetric synthesis; aza-Friedel–Crafts reaction; Carbohydrate auxiliaries; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Catalysis; Catalysts: preparations and properties; Chemistry; Chemistry, Organic; Exact sciences and technology; General and physical chemistry; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Indole; Lewis acid catalyzed; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Lewis acid catalyzed; aza-Friedel–Crafts reaction; Asymmetric synthesis; Indole; Carbohydrate auxiliaries; ENANTIOSELECTIVE SYNTHESIS; aza-Friedel-Crafts reaction; ALPHA; UGI-SYNTHESIS; STRECKER SYNTHESIS; TEMPLATES; DIASTEREOSELECTIVE SYNTHESIS; AMINO-ACIDS; N-TOSYL; STEREOSELECTIVE-SYNTHESIS; DERIVATIVES; Lewis acid; aza-Friedel―Crafts reaction; Nitrogen heterocycle; Oside; Chiral compound; Acid catalysis; Diastereoselectivity; Chiral auxiliary; Tin Compounds; Friedel Crafts reaction; Indole derivatives; Catalyst; Tin IV Chlorides
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2012.03.115

The diastereoselective formation of β-N-glycosidically linked 3-indolyl methanamine derivatives 5 has been achieved with high yield via an aza-Friedel–Crafts reaction. The reaction was performed by using O-pivaloylated galactosylamine 1 as a chiral template and SnCl4 combining TBAI as catalyst in DCM at −50°C. [Display omitted]