Organocatalytic one-pot asymmetric synthesis of 6-trifluoromethyl-substituted 7,8-dihydrochromen-6-ol

• Published in: Tetrahedron letters Vol. 95; p. 153733
• Main Authors: Nakashima, Kosuke, Minai, Asako, Okuaki, Yuichi, Matsushima, Yasuyuki, Hirashima, Shin-ichi, Miura, Tsuyoshi
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 13-04-2022
• Subjects: Asymmetric conjugate addition; Chromane; One-pot; Organocatalyst; One-pot; Chromane; Asymmetric conjugate addition; Organocatalyst
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2022.153733

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•A squaramide is a good catalyst for the asymmetric Friedel–Crafts alkylation of α,β-unsaturated trifluoromethyl ketones with aromatic alcohols in a one-pot procedure.•The first asymmetric synthesis of 6-trifluoromethyl-substituted 7, 8-dihydrochromen-6-ol derivatives.•The efficient one-pot procedure of chromane core is described.
A squaramide organocatalyst efficiently promoted the asymmetric Friedel–Crafts alkylation of α,β-unsaturated trifluoromethyl ketones with aromatic alcohols in a one-pot procedure, affording corresponding 6-trifluoromethyl-substituted 7,8-dihydrochromen-6-ol derivatives (up to 94% yield, 74% ee).