Stereocontrolled disruption of the Ugi reaction toward the production of chiral piperazinones: substrate scope and process development.
J Org Chem
; 79(21): 9948-57, 2014 Nov 07.
Article
em En
| MEDLINE
| ID: mdl-25254948
ABSTRACT
The factors determining diastereoselectivity observed in the multicomponent conversion of amino acids, aziridine aldehyde dimers, and isocyanides into chiral piperazinones have been investigated. Amino acid-dependent selectivity for either trans- or cis-substituted piperazinone products has been achieved. An experimentally determined diastereoselectivity model for the three-component reaction driven by aziridine aldehyde dimers has predictive value for different substrate classes. Moreover, this model is useful in reconciling the previously reported observations in multicomponent reactions between isocyanides, α-amino acids, and monofunctional aldehydes.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Aziridinas
/
Cianetos
/
Aldeídos
/
Dicetopiperazinas
/
Aminoácidos
Tipo de estudo:
Prognostic_studies
Idioma:
En
Ano de publicação:
2014
Tipo de documento:
Article