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

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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