Gold(III)-Catalyzed Propargylic Substitution Reaction Followed by Cycloisomerization for Synthesis of Poly-Substituted Furans from N-Tosylpropargyl Amines with 1,3-Dicarbonyl Compounds

Nobuyoshi Morita; Shingo Uchida; Hitomi Chiaki; Naho Ishii; Kentaro Tanikawa; Kosaku Tanaka III; Yoshimitsu Hashimoto; Osamu Tamura

doi:10.3390/molecules29020378

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Article

11 January 2024

Gold(III)-Catalyzed Propargylic Substitution Reaction Followed by Cycloisomerization for Synthesis of Poly-Substituted Furans from N-Tosylpropargyl Amines with 1,3-Dicarbonyl Compounds

and

Department of Pharmacy, Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida 194-8543, Japan

Research Foundation ITSUU Laboratory, C1232 Kanagawa Science Park R & D Building, 3-2-1 Sakado Takatsu-ku, Kawasaki 213-0012, Japan

Authors to whom correspondence should be addressed.

Molecules2024, 29(2), 378;https://doi.org/10.3390/molecules29020378

This article belongs to the Section Organic Chemistry

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Abstract

The treatment of N-tosylpropargyl amines 1 with 1,3-dicarbonyl compounds 2 in the presence of AuBr₃ (5 mol%) and AgOTf (15 mol%) afforded poly-substituted furans 3 in good-to-high yields via the gold-catalyzed cleavage of the sp³ carbon–nitrogen bond.

Keywords:

gold catalyst; poly-substituted furans; N-tosylpropargyl amines; propargylic substitution; cycloisomerization

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