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Asymmetric Synthesis of Diarylmethyl Sulfones by Palladium‐Catalyzed Enantioselective Benzylic Substitution: A Remarkable Effect of Water
Author(s) -
Najib Atifah,
Hirano Koji,
Miura Masahiro
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201800744
Subject(s) - enantioselective synthesis , catalysis , chemistry , substitution (logic) , palladium , binap , optically active , organic chemistry , computer science , programming language
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 H 2 O is found to be critical for high enantioselectivity.