Integrated Experimental and Computational Studies on the Organocatalytic Kinetic Resolution of ß-Unfunctionalized Primary Alcohols Using a Chiral 1,2-Diamine: The Importance of Noncovalent Interactions.
J Org Chem
; 87(6): 4468-4475, 2022 03 18.
Article
em En
| MEDLINE
| ID: mdl-35199522
ABSTRACT
The enantioselective kinetic resolution of ß-unfunctionalized primary alcohols with benzoyl chloride was carried out in the presence of a catalytic amount of a novel chiral 1,2-diamine derived from (S)-proline. Several valuable chiral 2-substituted propan-1-ols were obtained with good enantioselectivities. Density functional theory calculations revealed that the noncovalent interaction, such as CH-π interaction, is crucial for the enantioselectivity of the resolution. This study was conducted through an interplay between experiment and computation.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Diaminas
/
Álcoois
Idioma:
En
Ano de publicação:
2022
Tipo de documento:
Article