Regio- and stereochemical aspects in the functionalisation of a lithiated 2-(3-chloro-2-methyl-1-propenyl)-2-oxazoline: electrophile and temperature effects

Torna indietro

Abstract

4,4-Dimethyl-2-(3-chloro-2-methyl-1-propenyl)-2-oxazoline has been synthesized and deprotonated with LDA in THF to give the corresponding lithiated species, which has been found to react a-regioselectively with NH4Cl and alkyl halides, and g-regioselectively with carbonyl compounds to afford aprotonated (or a-alkyl-substituted) regioisomers and vinyl epoxides, respectively. The Z diastereoselectivity of both the protonation and the alkylation reactions was usually found to increase with the temperature. Ab initio calculations, performed on both the naked lithium salt and the corresponding solvated form, support the observed regioselectivity.

Autore Pugliese

Tutti gli autori

  • Rocchetti M.T. , Abbotto A. , Perna F.M. , Salomone A. , Florio S. , Capriati V.

Titolo volume/Rivista

TETRAHEDRON

Anno di pubblicazione

2015

ISSN

0040-4020

ISBN

Non Disponibile

Numero di citazioni Wos

Nessuna citazione

Ultimo Aggiornamento Citazioni

Non Disponibile

Numero di citazioni Scopus

Non Disponibile

0

Ultimo Aggiornamento Citazioni

28/04/2018

Settori ERC

Non Disponibile

Codici ASJC

Non Disponibile