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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Tandem Carbonyl-Alkyne Metathesis/Nucleophilic Cyclization of 1,2-Diketones with 2-Alkynyl-1,3-dithianes via Anion
Guohong Tang1, Xiaomeng Gong1, Yingying Xue1
1School of Pharmacy and State Key Laboratory of Natural Product Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.
Abstract:
Herein, we disclose a base-promoted tandem carbonyl-alkyne metathesis (CAM)/nucleophilic cyclization of 1,2-diketones with alkynyl-1,3-dithianes enabled by anion relay chemistry (ARC). This cascade process enables the regioselective synthesis of fully substituted 4-hydroxy-2-cyclopentenones under mild, one-pot conditions with broad substrate scope and excellent functional-group tolerance. The practicality of this protocol is demonstrated by gram-scale synthesis and diverse downstream derivatizations, highlighting the synthetic utility of the resulting cyclopentenone scaffolds.
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