Asymmetric Synthesis of Diarylmethyl Sulfones by Palladium‐Catalyzed Enantioselective Benzylic Substitution: A Remarkable Effect of Water. Issue 25 (14th April 2018)

• Record Type: Journal Article
• Authors: Najib, Atifah; Hirano, Koji; Miura, Masahiro
• Is Part Of: Chemistry. Volume 24:Issue 25(2018)
• Page Start: 6525
• Page End: 6529
• Publication Date: 2018-04-14
• Subjects: asymmetric catalysis -- benzylic substitution -- BINAP -- palladium -- sulfones; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201800744
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A Pd/( R )‐BINAP‐catalyzed enantioselective benzylic sulfonation of diarylmethyl carbonates with sodium sulfinates proceeds to deliver the corresponding chiral diarylmethyl sulfones in good yields with high enantioselectivity. The reaction occurs in a dynamic kinetic asymmetric transformation (DYKAT) manner and thus provides convergent access to optically active benzylic sulfones from racemic secondary benzylic carbonates. Additionally, the addition of H2 O is found to be critical for high enantioselectivity. Abstract : Dynamic road to sulfones : A Pd/( R )‐BINAP‐catalyzed enantioselective benzylic sulfonation of diarylmethyl carbonates with sodium sulfinates proceeds in a dynamic kinetic asymmetric transformation (DYKAT) to deliver the corresponding chiral diarylmethyl sulfones in good yields with high enantioselectivity. The key to success is the addition of H2 O as well as a judicious choice of chiral ancillary ligand.