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Palladium-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals.

ABSTRACT: Palladium(II) in combination with a monodentate phosphine ligand enables the unprecedented direct and ?-stereoselective catalytic synthesis of deoxyglycosides from glycals. Initial mechanistic studies suggest that in the presence of N-phenyl-2-(di-tert-butylphosphino)pyrrole as the ligand, the reaction proceeds via an alkoxy palladium intermediate that increases the proton acidity and oxygen nucleophilicity of the alcohol. The method is demonstrated with a wide range of glycal donors and acceptors, including substrates bearing alkene functionalities.

SUBMITTER: Sau A

PROVIDER: S-EPMC5484376 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

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Palladium-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals.

Sau Abhijit A Williams Ryan R Palo-Nieto Carlos C Franconetti Antonio A Medina Sandra S Galan M Carmen MC

Angewandte Chemie (International ed. in English) 20170217 13

Palladium(II) in combination with a monodentate phosphine ligand enables the unprecedented direct and α-stereoselective catalytic synthesis of deoxyglycosides from glycals. Initial mechanistic studies suggest that in the presence of N-phenyl-2-(di-tert-butylphosphino)pyrrole as the ligand, the reaction proceeds via an alkoxy palladium intermediate that increases the proton acidity and oxygen nucleophilicity of the alcohol. The method is demonstrated with a wide range of glycal donors and accepto ...[more]

PMID: 28211228

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