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Copper Reactivity Can be Tuned to Catalyse the Stereoselective Synthesis of 2-Deoxy Glycosides from Glycals

preprint
submitted on 07.08.2019 and posted on 07.08.2019 by Carlos Palo-Nieto, Abhijit Sau, Robin Jeanneret, Pierre-Adrien Payard, Maristela Braga Martins-Teixeira, Ivone Carvalho, Laurence Grimaud, M. Carmen Galan

We demonstrate that tuning the reactivity of Cu by the choice of oxidation state and counterion leads to the activation of both “armed” and “disarmed” type glycals towards direct glycosylation leading to the a-stereoselective synthesis of deoxyglycosides in good to excellent yields. Mechanistic studies show that CuI is essential for effective catalysis and stereocontrol and that the reaction proceeds through dual activation of both the enol ether as well as the OH nucleophile.

Funding

MCG, RJ and AS thank the European Research Council (ERCCOG: 648239) and CPN thanks RS Newton Fellowship. LG thanks the CNRS, the ENS/PSL and the ENS Paris Saclay (Ph.D. scholarship to P.-A.P.) for financial support. IC and MBMT thank Fundação de Amparo à Pesquisa do Estado de São Paulo - FAPESP Proc n. 2016/21194-6

History

Email Address of Submitting Author

m.c.galan@bristol.ac.uk

Institution

University of Bristol

Country

United Kingdom

ORCID For Submitting Author

0000-0001-7307-2871

Declaration of Conflict of Interest

No conflict of interest

Version Notes

first submission

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