Further studies on the [1,2]-Wittig rearrangement of 2-(2-benzyloxy)aryloxazolines
Abstract
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
ISSN
1420-3049Type
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
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