Kinetic Resolution of ß-Branched Aldehydes through Peptide-Catalyzed Conjugate Addition Reactions.
J Am Chem Soc
; 146(28): 19101-19107, 2024 Jul 17.
Article
em En
| MEDLINE
| ID: mdl-38960380
ABSTRACT
The catalytic kinetic resolution of racemic ß-branched aldehydes offers a straightforward stereoselective entry to aldehydes and addition products. Yet, control over stereoselectivity is difficult due to the conformational flexibility of ß-branched aldehydes. Here, we show that the peptide catalyst H-dPro-αMePro-Glu-NH2 resolves ß-branched aldehydes through reaction with nitroolefins and provides γ-nitroaldehydes with three consecutive stereogenic centers in high yields and stereoselectivities. Kinetic, NMR spectroscopic, and computational studies provided insights into the selectivity-determining step and origins of the kinetic resolution.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
J Am Chem Soc
Ano de publicação:
2024
Tipo de documento:
Article