Abstract
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.
Highlights
Palladium (II) in combination with a monodentate phosphine ligand enables the unprecedented direct and stereoselective catalytic synthesis of deoxyglycosides from glycals
Products resulting from addition of the proton and alkoxide nucleophile across the carbon-carbon double bond are formed when monodentate
N-phenyl-2-(di-tertbutylphosphino)pyrrole is employed as the ligand. This outcome is likely derived from an increase in affinity of palladium towards the OH nucleophile, which allows the reaction to proceed via an alkoxypalladation-type mechanism to yield the glycoside with high -stereocontrol
Summary
Link to publication record in Explore Bristol Research PDF-document. This is the author accepted manuscript (AAM). Please refer to any applicable terms of use of the publisher. General rights This document is made available in accordance with publisher policies. Please cite only the published version using the reference above. Full terms of use are available: http://www.bristol.ac.uk/red/research-policy/pure/user-guides/ebr-terms/. Palladium-Catalysed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals.
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