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

被引：5
作者：
Aitken, R. Alan [1 ]
Harper, Andrew D. [1 ]
Inwood, Ryan A. [1 ]
机构：
[1] Univ St Andrews, EaStCHEM Sch Chem, St Andrews KY16 9ST, Fife, Scotland
来源：
MOLECULES | 2022年 / 27卷 / 10期
基金：
英国工程与自然科学研究理事会;
关键词：
oxazoline; Wittig rearrangement; phthalide; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; SYNTHETIC UTILITY; AMINO-ACIDS; CYCLIZATION; OXAZOLINES; PHTHALIDES; GLYCOSIDES; COMPLEXES; CHEMISTRY;
D O I：
10.3390/molecules27103186
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
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.
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页数：23
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