Asymmetric Friedel−Crafts Alkylation of Indoles with α, β‐unsaturated Trifluoromethyl Ketones Using a Squaramide Organocatalyst. Issue 10 (8th September 2022)

• Record Type: Journal Article
• Authors: Nakashima, Kosuke; Hanamura, Sumire; Imamura, Aoi; Matsushima, Yasuyuki; Hirashima, Shin‐ichi; Miura, Tsuyoshi
• Is Part Of: Asian journal of organic chemistry. Volume 11:Issue 10(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-09-08
• Subjects: asymmetric reactions -- squaramide -- indole -- Friedel−Crafts alkylation -- spiro indoline 3-one; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202200403
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: This study explores the asymmetric Friedel−Crafts alkylation of indoles with α, β‐unsaturated trifluoromethyl ketones using a squaramide organocatalyst. The squaramide organocatalyst efficiently promoted the asymmetric Friedel−Crafts alkylation of indoles with α, β‐unsaturated trifluoromethyl ketones, affording the corresponding products bearing both indole motif and trifluoromethyl group in high yields with excellent enantioselectivities (up to 99% ee). The transformation of the obtained adduct to chiral spiro indoline 3‐one was also demonstrated. Abstract : The squaramide organocatalyst efficiently promoted the asymmetric Friedel−Crafts alkylation of indoles with α, β‐unsaturated trifluoromethyl ketones, affording the corresponding products bearing both indole motif and trifluoromethyl group in high yields with excellent enantioselectivities (up to 99% ee ).