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

Alexander S Henderson, John F Bower, M Carmen Galan

Research output: Contribution to journalArticle (Academic Journal)peer-review

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.

Original languageEnglish
Pages (from-to)3012-3016
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume18
Issue number16
DOIs
Publication statusPublished - 29 Apr 2020

Structured keywords

  • BCS and TECS CDTs

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