Stereoselection in the Betti reaction of valine methyl esters
Abstract
The multi-component Betti reaction of 2-naphthol, benzaldehyde and (S)-amines, that usually provides highly valuable aminobenzylnaphthol bearing two stereogenic centers, yielded a completely racemic product, when (S)-valine methyl ester was employed as the amine in the usual reaction protocol. The cause of this drawback, that appears to be overlooked in the literature, was investigated. As a result, new reaction conditions were set up, that were able to yield the expected useful product, having two fully resolved stereogenic centers. Furthermore, when the effect of substituents on the phenyl ring was preliminarily studied, we found that 4-fluoro- and 4-chlorobenzaldeyde gave stereoisomerically pure compounds also in the original reaction protocol.
Autore Pugliese
Tutti gli autori
-
CARDELLICCHIO C.;CAPOZZI M.A.M.
Titolo volume/Rivista
Non Disponibile
Anno di pubblicazione
2017
ISSN
0957-4166
ISBN
Non Disponibile
Numero di citazioni Wos
Nessuna citazione
Ultimo Aggiornamento Citazioni
Non Disponibile
Numero di citazioni Scopus
1
Ultimo Aggiornamento Citazioni
Non Disponibile
Settori ERC
Non Disponibile
Codici ASJC
Non Disponibile
Condividi questo sito sui social