Asymmetric Synthesis of Diarylmethyl Sulfones by Palladium‐Catalyzed Enantioselective Benzylic Substitution: A Remarkable Effect of Water | Zendy

Najib Atifah | Zendy; Hirano Koji | Zendy; Miura Masahiro | Zendy

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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.

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