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Practical and Scalable Kinetic Resolution of BINOLs Mediated by a Chiral Counterion.

ABSTRACT: BINOLs are valuable and widely used building blocks, chiral ligands, and catalysts that are effective across a remarkable range of different chemical transformations. Here we demonstrate that an ammonium salt catalyzed kinetic resolution of racemic BINOLs with benzyl tosylate proceeds with s up to 46. This is a scalable and practical process that can be applied across >30 different C2 - and non-C2 -symmetric BINOLs. Implementation of this method enables the enantioselective synthesis of a wide range of BINOL derivatives with over 99:1 e.r.

SUBMITTER: Jones BA

PROVIDER: S-EPMC6492193 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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Practical and Scalable Kinetic Resolution of BINOLs Mediated by a Chiral Counterion.

Jones Benjamin A BA Balan Tudor T Jolliffe John D JD Campbell Craig D CD Smith Martin D MD

Angewandte Chemie (International ed. in English) 20190305 14

BINOLs are valuable and widely used building blocks, chiral ligands, and catalysts that are effective across a remarkable range of different chemical transformations. Here we demonstrate that an ammonium salt catalyzed kinetic resolution of racemic BINOLs with benzyl tosylate proceeds with s up to 46. This is a scalable and practical process that can be applied across >30 different C<sub>2</sub> - and non-C<sub>2</sub> -symmetric BINOLs. Implementation of this method enables the enantioselective ...[more]

PMID: 30779415

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