Asymmetric Synthesis of Multi-Substituted Tetrahydrofurans via Palladium/Rhodium Synergistic Catalyzed [3+2] Decarboxylative Cycloaddition of Vinylethylene Carbonates.
Unlike the comprehensive development of tandem multi-metallic catalysis, bimetallic synergistic catalysis has been challenging to achieve high stereoselectivity with the generation of multi-stereogenic centers. Herein, an efficient synergistic catalysis for the diastereo- and enantioselective synthesis of multi-substituted tetrahydrofuran derivatives has been developed. Under mild reaction conditions, a series of target molecules with three consecutive stereocenters were synthesized by a palladium(0)/rhodium(III) bimetal-catalyzed asymmetric decarboxylative [3+2]-cycloaddition of vinylethylene carbonates with α,β-unsaturated carbonyl compounds. The corresponding adducts were obtained with moderate to high yields (67 %∼98 %) and excellent stereoselectivities (>20 : 1 d.r., up to 99 % ee).
['Ming|Siliang|S|', 'Qurban|Saira|S|', 'Du|Yu|Y|http://orcid.org/0000-0003-2287-5265', 'Su|Weiping|W|']
D002254:Carbonates D002384:Catalysis D061565:Cycloaddition Reaction D005663:Furans D010165:Palladium D012238:Rhodium D013237:Stereoisomerism
multi-substituted tetrahydrofurans cycloaddition synergistic catalysis asymmetric catalysis bimetallic catalysis