Palladium-Catalyzed Decarboxylative Cycloaddition of Vinylethylene Carbonates with Formaldehyde: Enantioselective Construction of Tertiary Vinylglycols†
Ajmal Khan
School 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)
Search for more papers by this authorDr. Renfeng Zheng
School 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)
Search for more papers by this authorProf. Dr. Yuhe Kan
Jiangsu Key Laboratory for Chemistry of Low-Dimensional, Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huaian 223300 (P. R. China)
Search for more papers by this authorJiang Ye
School 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)
Search for more papers by this authorJuxiang Xing
School 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)
Search for more papers by this authorCorresponding Author
Prof. Dr. Yong Jian Zhang
School 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)
School 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)Search for more papers by this authorAjmal Khan
School 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)
Search for more papers by this authorDr. Renfeng Zheng
School 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)
Search for more papers by this authorProf. Dr. Yuhe Kan
Jiangsu Key Laboratory for Chemistry of Low-Dimensional, Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huaian 223300 (P. R. China)
Search for more papers by this authorJiang Ye
School 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)
Search for more papers by this authorJuxiang Xing
School 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)
Search for more papers by this authorCorresponding Author
Prof. Dr. Yong Jian Zhang
School 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)
School 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)Search for more papers by this authorThis work was supported by the Innovation Program of Shanghai Municipal Education Commission (14ZZ023), National Key Basic Research Program of China (2013CB934101), Shanghai Pujiang Program (11PJD012), and Shanghai Jiao Tong University. We thank the Instrumental Analysis Center of Shanghai Jiao Tong University for HRMS analysis.
Graphical Abstract
A Pd complex: An efficient method for the enantioselective construction of tertiary vinylglycols by the title reaction was developed. The palladium complex generated from [Pd2(dba)3]⋅CHCl3 and L catalyzes the cycloaddition under mild reaction conditions, thus converting racemic 1 into the corresponding 1,3-dioxolanes 2 in high yields with good to excellent enantioselectivities. dba=dibenzylideneacetone.
Abstract
An efficient method for the enantioselective construction of tertiary vinylglycols through a palladium-catalyzed asymmetric decarboxylative cycloaddition of vinylethylene carbonates with formaldehyde was developed. By using a palladium complex generated in situ from [Pd2(dba)3]⋅CHCl3 and a phosphoramidite ligand as a catalyst under mild reaction conditions, the process allows conversion of racemic 4-substituted 4-vinyl-1,3-dioxolan-2-ones into the corresponding 1,3-dioxolanes, as methylene acetal protected tertiary vinylglycols, in high yields with good to excellent enantioselectivities.
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