C7‐Functionalization of Indoles via Organocatalytic Enantioselective Friedel‐Crafts Alkylation of 4‐Amino‐ indoles with 2‐Butene‐1, 4‐diones and 3‐Aroylacrylates. Issue 15 (1st July 2019)

• Record Type: Journal Article
• Authors: Huang, Tongkun; Zhao, Yunlong; Meng, Shanshui; Chan, Albert S. C.; Zhao, Junling
• Is Part Of: Advanced synthesis & catalysis. Volume 361:Issue 15(2019)
• Page Start: 3632
• Page End: 3638
• Publication Date: 2019-07-01
• Subjects: C7-Friedel-Crafts reaction -- Organocatalysis -- Indole -- Enantioselectivity -- Regioselectivity; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201900377
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: An efficient protocol for the enantioselective C7 Friedel‐Crafts alkylation between 4‐aminoindoles and 2‐butene‐1, 4‐diones or 3‐aroylacrylates was reported. This process was catalyzed by a chiral phosphoric acid, affording the corresponding 1, 4‐disubstituted indoles in moderate to high yields with good to high enantioselectivities. This reaction could be performed on a gram scale without loss of efficiency, and a representative derivatization of the products was also investigated to prepare the corresponding C3 formylation compound. Abstract :