Further studies on the [1,2]-Wittig rearrangement of 2-(2-benzyloxy)aryloxazolines

The behaviour of 14 ortho-functionalised 2-aryloxazolines, 11 of them prepared and characterised for the first time, with butyllithium has been examined. Significant limitations to the Wittig rearrangement of such systems are revealed. In terms of asymmetric Wittig rearrangement, good diastereoselectivity is obtained with a valine-derived 4-isopropyl oxazoline but this is compromised by racemisation upon hydrolysis. More encouraging selectivity is achieved in the Wittig rearrangement of an acyclic phenylalanine-derived ortho-benzyloxy benzamide.

Citation

Aitken , R A , Harper , A D & Inwood , R 2022 , ' Further studies on the [1,2]-Wittig rearrangement of 2-(2-benzyloxy)aryloxazolines ' , Molecules , vol. 27 , no. 10 , 3186 . https://doi.org/10.3390/molecules27103186

Publication

Molecules

Status

Peer reviewed

DOI

https://doi.org/10.3390/molecules27103186

ISSN

1420-3049

Type

Journal article

Rights

Copyright © 2022 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).

Description

Authors thank EPSRC (UK) for a DTA studentship to ADH (Grant EP/L505079/1), EPSRC (UK) and CRITICAT Centre for Doctoral Training for a studentship to R. A. I. (Grant code: EP/L016419/1) and the EPSRC UK National Mass Spectrometry Facility at Swansea University.

Collections

University of St Andrews Research

URI

http://hdl.handle.net/10023/25389