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Updated: Apr 20, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Palladium-catalyzed enantioselective decarboxylative cycloaddition of vinylethylene carbonates with isocyanates
Ajmal Khan1, Juxiang Xing, Jingming Zhao
1School of Chemistry and Chemical Engineering and Shanghai Key Laboratory of Electrical Insulation and Thermal Aging, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240 (P. R. China), Fax: (+86) 21-5474-1297.
Abstract:
An efficient method for the enantioselective construction of β-substituted β-vinylglycinol derivatives through palladium-catalyzed decarboxylative cycloaddition of vinylethylene carbonates with isocyanates was developed. By using a palladium complex generated in situ from [Pd2 (dba)3]⋅CHCl3 (dba=dibenzylideneacetone) and (S)-Segphos as a catalyst under mild reaction conditions, the process provided 4-substituted-4-vinyloxazolidin-2-ones in high yields with a high level of enantioselectivity. The stereochemical outcome of the reaction was explained by DFT calculations and the synthetic utility of the process was demonstrated by the gram-scale transformation and formal synthesis of MK-0731 as a kinesin spindle protein inhibitor.
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