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Highly Diastereoselective Synthesis of

Lisi Yuan¹, Ya Fang¹, Zhaobo Zhou¹

¹State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou, Gansu 730000, P. R. China.

Organic Letters

|June 5, 2023

Summary

This study introduces a new method for creating C-hydroxymethine glycosides using a chiral N-heterocyclic carbene-copper catalyst. This efficient synthesis offers high diastereoselectivity for diverse glycoside production.

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Area of Science:

Organic Chemistry
Carbohydrate Chemistry
Catalysis

Background:

C-hydroxymethine glycosides are important structural motifs in biologically active compounds.
Developing efficient and stereoselective synthetic routes to these compounds remains a challenge.

Purpose of the Study:

To develop a highly diastereoselective synthesis of C-hydroxymethine glycosides.
To utilize glycal anomers and a chiral N-heterocyclic carbene-copper catalyst for this synthesis.

Main Methods:

Employing a chiral N-heterocyclic carbene-copper catalyst for the reaction between glycal anomers and functionalized aldehydes.
Investigating the synergistic control of diastereoselectivity by substrate stereocenter and catalyst chirality.

Main Results:

Achieved a highly diastereoselective synthesis of C-hydroxymethine glycosides.
Demonstrated that stereochemistry at C5 and the anomeric position did not impede the high diastereoselectivity.
Showcased the versatility of the approach with various functionalized aldehydes.

Conclusions:

The developed method provides an efficient and stereoselective route to diverse C-hydroxymethine glycosides.
The chiral N-heterocyclic carbene-copper catalyst plays a crucial role in controlling diastereoselectivity.
This approach expands the synthetic accessibility of valuable glycoside derivatives.