The 5(S)-((3aR,4R,6aR)-2,2-Dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-phenyl-4,5-dihydrooxazole

被引：0
|
作者：
Boiaryna, Liliana [1 ]
Guillarme, Stephane [1 ]
Saluzzo, Christine [1 ]
机构：
[1] Le Mans Univ, Inst Mol & Mat Mans IMMM, MSO, UMR 6283,CNRS, Ave O Messiaen, F-72085 Le Mans, France
来源：
MOLBANK | 2024年 / 2024卷 / 03期
关键词：
chiral oxazoline; isosorbide; isohexide; sustainable material; epoxide; nitrile; carbohydrate; biomass; OXAZOLINE-CONTAINING LIGANDS;
D O I：
10.3390/M1843
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
5(S)-((3aR,4R,6aR)-2,2-Dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-phenyl-4,5-dihydrooxazole was synthesized from isosorbide in a three-step sequence, with an overall yield of 46%. The first reaction step involves a single regioselective ring-opening reaction of isosorbide with Me3SiI in the presence of acetone followed by an intramolecular nucleophilic substitution to transform the iodoalcohol into its corresponding epoxide. The last reaction allows the formation of the oxazoline ring directly from the epoxide with benzonitrile in the presence of BF3<middle dot>Et2O.
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页数：3
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