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Palladium‐Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals
Author(s) -
Sau Abhijit,
Williams Ryan,
PaloNieto Carlos,
Franconetti Antonio,
Medina Sandra,
Galan M. Carmen
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201612071
Subject(s) - chemistry , palladium , stereoselectivity , nucleophile , alkene , catalysis , ligand (biochemistry) , phosphine , denticity , glycal , combinatorial chemistry , organic chemistry , medicinal chemistry , biochemistry , receptor , crystal structure
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 acceptors, including substrates bearing alkene functionalities.