Issue 9, 2022

Organocatalyzed trifunctionalization of alkynyl 1,2-diones for the concise synthesis of acyloxy allylidene malonates and γ-alkylidenebutenolides

Abstract

Two types of unprecedented organic phosphine-catalyzed trifunctionalization of ynones have been achieved under mild and environmentally benign conditions using iPrOH as the solvent, delivering a range of synthetically valuable acyloxy allylidene malonates and γ-alkylidenebutenolides in good yields with high stereoselectivities. A series of uncommon bond cleavage and bond formation processes have been observed in the reactions, showing the robustness of organocatalysis in facilitating complicated transformations. Mechanistic studies indicate that iPrOH plays a dual role as both the solvent and the reactant.

Graphical abstract: Organocatalyzed trifunctionalization of alkynyl 1,2-diones for the concise synthesis of acyloxy allylidene malonates and γ-alkylidenebutenolides

Supplementary files

Article information

Article type
Communication
Submitted
06 janv. 2022
Accepted
14 mars 2022
First published
15 mars 2022

Green Chem., 2022,24, 3623-3628

Organocatalyzed trifunctionalization of alkynyl 1,2-diones for the concise synthesis of acyloxy allylidene malonates and γ-alkylidenebutenolides

L. Chen, S. Niu, S. Lan, W. Liu, S. Yang and X. Fang, Green Chem., 2022, 24, 3623 DOI: 10.1039/D2GC00061J

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