Palladium-Catalyzed Asymmetric Decarboxylative Cycloaddition of Vinylethylene Carbonates with Electrophiles: Construction of Quaternary Stereocenters

Ajmal Khan; Yong Jian Zhang

doi:10.1055/s-0034-1380170

Synlett, Table of Contents

Synlett 2015; 26(07): 853-860
DOI: 10.1055/s-0034-1380170

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Palladium-Catalyzed Asymmetric Decarboxylative Cycloaddition of Vinylethylene Carbonates with Electrophiles: Construction of Quaternary Stereocenters

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. of China Email: yjian@sjtu.edu.cn

,

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. of China Email: yjian@sjtu.edu.cn

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Abstract

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Abstract

The enantioselective construction of quaternary stereocenters still remains significant challenge in organic synthesis. Herein, an efficient synthetic strategy for the construction of quaternary stereocenters via palladium-catalyzed asymmetric decarboxylative cycloaddition of vinylethylene carbonates (VEC) with unsaturated electrophiles is highlighted. The processes that enable rapid access to methylene acetal protected tertiary vinylglycols, carbonyl-protected β-substituted β-vinylglycinols, and multifunctionalized tetrahydrofurans bearing continuous tertiary and vicinal all-carbon quaternary stereocenters in high yields with high levels of stereoselectivities.

Key words

asymmetric catalysis - quaternary stereocenters - palladium - decarboxylative cycloaddition - vinylethylene carbonates

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References

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