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

R Alan Aitken; Andrew D. Harper; Ryan Inwood

doi:10.3390/molecules27103186

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

R Alan Aitken^*, Andrew D. Harper, Ryan Inwood

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

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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.

Original language	English
Article number	3186
Number of pages	23
Journal	Molecules
Volume	27
Issue number	10
DOIs	https://doi.org/10.3390/molecules27103186
Publication status	Published - 17 May 2022

Keywords

Oxazoline
Wittig rearrangement
Phthalide

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10.3390/molecules27103186Licence: CC BY

molecules-27-03186
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/).
Final published version, 2.34 MBLicence: CC BY

CRITICAT - Delivery of Teach & Training: CRITICAT - Delivery of Teaching & Technical Training
Smith, A. D. (PI)
EPSRC
1/05/14 → 31/10/22
Project: Standard

Further studies on the [1,2]-Wittig rearrangement of 2-(2-benzyloxy)aryloxazolines (dataset)
Aitken, R. A. (Creator), Harper, A. D. (Creator) & Inwood, R. (Creator), University of St Andrews, 28 May 2022
DOI: 10.17630/8f4fe556-b101-4768-814e-668472c0c7a2
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title = "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.",

keywords = "Oxazoline, Wittig rearrangement, Phthalide",

author = "Aitken, {R Alan} and Harper, {Andrew D.} and Ryan Inwood",

note = "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.",

year = "2022",

month = may,

day = "17",

doi = "10.3390/molecules27103186",

language = "English",

volume = "27",

journal = "Molecules",

issn = "1420-3049",

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TY - JOUR

T1 - Further studies on the [1,2]-Wittig rearrangement of 2-(2-benzyloxy)aryloxazolines

AU - Aitken, R Alan

AU - Harper, Andrew D.

AU - Inwood, Ryan

N1 - 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.

PY - 2022/5/17

Y1 - 2022/5/17

N2 - 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.

AB - 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.

KW - Oxazoline

KW - Wittig rearrangement

KW - Phthalide

U2 - 10.3390/molecules27103186

DO - 10.3390/molecules27103186

M3 - Article

SN - 1420-3049

VL - 27

JO - Molecules

JF - Molecules

IS - 10

M1 - 3186

ER -

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

Abstract

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Projects

CRITICAT - Delivery of Teach & Training: CRITICAT - Delivery of Teaching & Technical Training

Datasets

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

Cite this