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.


Tutti gli autori

  • CARDELLICCHIO C.;CAPOZZI M.A.M.

Titolo volume/Rivista

Non Disponibile


Anno di pubblicazione

2017

ISSN

0957-4166

ISBN

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Numero di citazioni Wos

Nessuna citazione

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Numero di citazioni Scopus

1

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Settori ERC

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Codici ASJC

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