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 Janv. 2020
Accepted
05 Febr. 2020
First published
08 Apr. 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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