Synthesis 2019; 51(22): 4215-4230
DOI: 10.1055/s-0037-1611916
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed One-Pot Stereospecific Synthesis of 2-Deoxy Aryl C-Glycosides from Glycals and Anilines in the Presence of tert-Butyl Nitrite

Adesh Kumar Singh
,
Rapelly Venkatesh
,
Department of Chemistry, Indian Institute of Technology (BHU), Varanasi, Uttar Pradesh, 221005, India   Email: jeyakumar.chy@iitbhu.ac.in
› Author Affiliations
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 (eFirst)

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.

Supporting Information

 
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