Further Studies on the [1,2]-Wittig Rearrangement of 2-(2-Benzyloxy)aryloxazolines

R Alan Aitken; Andrew D Harper; Ryan A Inwood

doi:10.3390/molecules27103186

Further Studies on the [1,2]-Wittig Rearrangement of 2-(2-Benzyloxy)aryloxazolines

Molecules. 2022 May 17;27(10):3186. doi: 10.3390/molecules27103186.

Authors

R Alan Aitken¹, Andrew D Harper¹, Ryan A Inwood¹

Affiliation

¹ EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews KY16 9ST, Fife, UK.

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: Wittig rearrangement; oxazoline; phthalide.

MeSH terms

Stereoisomerism*

Abstract

MeSH terms

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