Borane promoted aryl transfer reaction for the synthesis of α-aryl functionalised β-hydroxy and β-keto esters

The synthesis of a series of α-aryl or α-alkyl functionalised β-hydroxy and β-keto esters has been achieved by reacting α-diazoesters with boranes, and aldehydes, ketones, anhydrides, nitriles, esters or isocyanates. In a mild reaction protocol, 26 examples are presented in yields up to 73%. The syn...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2022-06, Vol.2 (21), p.4298-432
Main Authors: Kaehler, Tanja, Lorenz, Jonas, Ould, Darren M. C, Engl, Dorothea, Santi, Micol, Gierlichs, Lukas, Wirth, Thomas, Melen, Rebecca L
Format: Article
Language:English
Subjects:
Aldehydes
Aromatic compounds
Boranes
Chemical synthesis
Cyanide
Esters
Isocyanates
Ketones
Nitriles
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Summary:The synthesis of a series of α-aryl or α-alkyl functionalised β-hydroxy and β-keto esters has been achieved by reacting α-diazoesters with boranes, and aldehydes, ketones, anhydrides, nitriles, esters or isocyanates. In a mild reaction protocol, 26 examples are presented in yields up to 73%. The synthesis of a series of α-aryl or α-alkyl functionalised β-hydroxy and β-keto esters has been achieved by reacting α-diazoesters with boranes, and aldehydes, ketones, anhydrides, nitriles, esters or isocyanates.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob00643j