Synlett 2015; 26(07): 853-860
DOI: 10.1055/s-0034-1380170
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© Georg Thieme Verlag Stuttgart · New York

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
› Author Affiliations
Further Information

Publication History

Received: 06 December 2014

Accepted after revision: 12 January 2015

Publication Date:
12 February 2015 (online)

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.

 
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