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Synthesis 2019; 51(22): 4215-4230
DOI: 10.1055/s-0037-1611916
DOI: 10.1055/s-0037-1611916
paper
Palladium-Catalyzed One-Pot Stereospecific Synthesis of 2-Deoxy Aryl C-Glycosides from Glycals and Anilines in the Presence of tert-Butyl Nitrite
J.K. acknowledges the Department of Science and Technology, India (DST-India) (DST/INT/MPG/P-09/2016) and the Max-Planck Society, Germany for financial support through an Indo-Max Planck partner group project. A.K.S. acknowledges the Council of Scientific and Industrial Research (CSIR) for a senior research fellowship [File No: 09/1217(0005/2015-EMR-I]. R.V. is grateful to the Indian Institute of Technology (IIT) (BHU) for a research fellowship.Further Information
Publication History
Received: 22 June 2019
Accepted after revision: 08 August 2019
Publication Date:
26 August 2019 (online)
Abstract
The palladium-catalyzed one-pot synthesis of 2,3-deoxy-3-keto aryl C-glycosides is achieved from glycals and anilines in the presence of tert-butyl nitrite and aqueous HBF4 under mild conditions. This one-pot method stereospecifically provides α- and β-aryl glycosides (≥19:1 by NMR) in good yields at room temperature. The configuration at the C-3 position in the glycal determines the anomeric selectivity (i.e., α or β) of the desired products.
Key words
palladium - C-glycosylation - aryldiazonium salts - stereospecific - tert-butyl nitrite - anilinesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611916.
- Supporting Information
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