Ligand‐Controlled Stereoselective Synthesis of 2‐Deoxy‐β‐C‐glycosides by Cobalt Catalysis

Author:

Liu Bingxue1,Liu Deguang2,Rong Xianle1,Lu Xi2,Fu Yao2,Liu Qiang1ORCID

Affiliation:

1. Center of Basic Molecular Science (CBMS) Department of Chemistry Tsinghua University 100084 Beijing China

2. School of Chemistry and Materials Science CAS Key Laboratory of Urban Pollutant Conversion Anhui Province Key Laboratory of Biomass Clean Energy University of Science and Technology of China 230026 Hefei China

Abstract

Abstract2‐Deoxy‐β‐C‐glycosides represent an important class of carbohydrates that are present in many bioactive molecules. However, owing to the lack of substituents at the C2 position, the stereoselective synthesis of 2‐deoxy‐β‐C‐glycosides is highly challenging. Herein, we report a ligand‐controlled stereoselective C‐alkyl glycosylation reaction to access 2‐deoxy‐β‐C‐alkyl glycosides from readily available glycals and alkyl halides. This method exhibits broad substrate scope and excellent diastereoselectivity under very mild conditions. In addition, unprecedented stereodivergent synthesis of 2‐deoxy‐C‐ribofuranosides is achieved using different chiral bisoxazoline ligands. Mechanistic studies suggest that hydrometallation of the glycal with the bisoxazoline‐ligated Co−H species may be the turnover‐limiting and stereodetermining step of this transformation.

Funder

National Natural Science Foundation of China

Publisher

Wiley

Subject

General Chemistry,Catalysis

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