Issue 16, 2020

Pseudo-enantiomeric carbohydrate-based N-heterocyclic carbenes as promising chiral ligands for enantiotopic discrimination

Abstract

The practical synthesis of carbohydrate-based NHC–Rh complexes bearing C1 or C3 sterically differentiated positions, accessed by glycosylation or SNAr strategies, is reported. These catalysts exhibit pseudo-enantiomeric behaviour in the hydrosilylation of acetophenone. We show that steric bulk at C1 gives preference for (S)-phenyl-1-ethanol, while bulk at C3 leads to the (R)-enantiomer. These results represent the first example of pseudo-enantiomeric carbohydrate-based NHC ligands leading to enantiotopic discrimination.

Graphical abstract: Pseudo-enantiomeric carbohydrate-based N-heterocyclic carbenes as promising chiral ligands for enantiotopic discrimination

Supplementary files

Article information

Article type
Communication
Submitted
23 1 2020
Accepted
05 2 2020
First published
08 4 2020

Org. Biomol. Chem., 2020,18, 3012-3016

Pseudo-enantiomeric carbohydrate-based N-heterocyclic carbenes as promising chiral ligands for enantiotopic discrimination

A. S. Henderson, J. F. Bower and M. C. Galan, Org. Biomol. Chem., 2020, 18, 3012 DOI: 10.1039/D0OB00155D

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