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Gold-Catalyzed Oxidative Reactions of Propargylic Carbonates Involving 1,2-Carbonate Migration: Stereoselective Synthesis of Functionalized Alkenes

Ning Sun, Ming Chen and Yuanhong Liu*

*State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, People’s Republic of China, Email: yhliumail.sioc.ac.cn

N. Sun, M. Chen, Y. Liu, J. Org. Chem., 2014, 79, 4055-4067.

DOI: 10.1021/jo500573s (free Supporting Information)


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Abstract

A gold-catalyzed oxidative reaction of propargylic carbonates or acetates using 3,5-dichloropyridine as the oxidant provides efficient access to α-functionalized-α,β-unsaturated ketones with excellent regio- and diastereocontrol. In addition, these alkene products could be further transformed into valuable 5-hydroxycyclopent-2-enones via cyclocondensation with acetone or cyclodimerization under basic conditions.

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Key Words

cyclopentenones


ID: J42-Y2014