| Title: | Oxidative Asymmetric Aza-Friedel-Crafts Alkylation of Indoles with 3-Indolinone-2-carboxylates Catalyzed by a BINOL Phosphoric Acid and Promoted by DDQ |
| Author(s): | Yarlagadda S; Sridhar B; Subba Reddy BV; |
| Address: | "Centre for Semiochemicals, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500007, India. Laboratory of X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500007, India" |
| ISSN/ISBN: | 1861-471X (Electronic) 1861-471X (Linking) |
| Abstract: | "An asymmetric aza-Friedel-Crafts alkylation reaction between indoles and indolenines that were derived in situ from 3-indolinone-2-carboxylates has been developed by using 3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate as a catalyst. The reaction proceeded under mild conditions and provided chiral indol-3-yl-3-indolinone-2-carboxylate derivatives in good yields with excellent ee values (up to 98.6 %). Similarly, the Mannich-type addition of indoline-3-ones to indolenines provided heterodimers with vicinal chiral quaternary centers. This method was successfully applied to the construction of the core structure of trigonoliimine C" |
| Keywords: | Mannich reaction alkylation asymmetric synthesis indoles synthetic methods; |
| Notes: | "PubMed-not-MEDLINEYarlagadda, Suresh Sridhar, B Subba Reddy, Basireddy Venkata eng Germany 2018/03/27 Chem Asian J. 2018 May 18; 13(10):1327-1334. doi: 10.1002/asia.201800300. Epub 2018 Apr 25" |
