Asymmetric Synthesis of Multi‐Substituted Tetrahydrofurans via Palladium/Rhodium Synergistic Catalyzed [3+2] Decarboxylative Cycloaddition of Vinylethylene Carbonates. Issue 50 (22nd July 2021)

• Record Type: Journal Article
• Authors: Ming, Siliang; Qurban, Saira; Du, Yu; Su, Weiping
• Is Part Of: Chemistry. Volume 27:Issue 50(2021)
• Page Start: 12742
• Page End: 12746
• Publication Date: 2021-07-22
• Subjects: asymmetric catalysis -- bimetallic catalysis -- cycloaddition -- multi-substituted tetrahydrofurans -- synergistic catalysis; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202102024
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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). Abstract : Multimetallic cooperative catalysis represents one of the most efficient method for asymmetric C−C and C‐heteroatom bond forming transformations. An enantioselective [3+2] cycloaddition reaction catalyzed synergistically by the combination of an achiral palladium catalyst and a chiral‐at‐metal rhodium(III) complex has been developed, generating a series of 1, 2, 3, 3‐tetrasubstituted tetrahydrofurans in high yields and stereoselectivities (>20 : 1 d.r., up to 99 % ee).