Asymmetric synthesis of CF3- and indole-containing tetrahydro-β-carbolines via chiral spirocyclic phosphoric acid-catalyzed aza-Friedel–Crafts reaction. Issue 7 (26th April 2017)

• Record Type: Journal Article
• Authors: Xie, En; Rahman, Abdul; Lin, Xufeng
• Is Part Of: Organic chemistry frontiers. Volume 4:Issue 7(2017)
• Page Start: 1407
• Page End: 1410
• Publication Date: 2017-04-26
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c7qo00229g
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : An enantioselective aza-Friedel–Crafts reaction of indoles with 1-trifluoromethyl-3, 4-dihydro-β-carbolines has been developed to afford tetrahydro-β-carbolines with a CF3 - and indole-containing quaternary stereocenter by using chiral phosphoric acid catalysis. Abstract : An enantioselective aza-Friedel–Crafts alkylation reaction of indoles with 1-trifluoromethyl-3, 4-dihydro-β-carbolines catalyzed by a chiral spirocyclic phosphoric acid has been realized. This methodology provides a facile route to 1-trifluoromethyl-1-indole-substituted tetrahydro-β-carbolines featuring a CF3 -containing quaternary stereocenter in considerable yields and good enantioselectivities.