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 3rd; Yoshimitsu Hashimoto; Osamu Tamura

doi:10.3390/molecules29020378

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

Molecules. 2024 Jan 11;29(2):378. doi: 10.3390/molecules29020378.

Authors

Nobuyoshi Morita¹, Shingo Uchida¹, Hitomi Chiaki¹, Naho Ishii¹, Kentaro Tanikawa¹, Kosaku Tanaka 3rd^{1

2}, Yoshimitsu Hashimoto¹, Osamu Tamura¹

Affiliations

¹ Department of Pharmacy, Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida 194-8543, Japan.
² Research Foundation ITSUU Laboratory, C1232 Kanagawa Science Park R & D Building, 3-2-1 Sakado Takatsu-ku, Kawasaki 213-0012, Japan.

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

Grants and funding

20 K05517/Japan Society for the Promotion of Science