A facile stereoselective synthesis of 2-perfluoroalkyl-3a,4,5,6-tetrahydroimidazo[1,5- b]isoxazoles

2-Perfluoroalkyl-3a,4,5,6-tetrahydroimidazo[1,5- b]isoxazoles 3 were obtained in good yields with high diastereoselectivity and regioselectivity via the reaction of excess methyl 2-perfluoroalkynoates 2 with cyclic nitrones 1 via 1,3-dipolar cycloaddition. ▪ Methyl 2-perfluoroalkynoates 2 reacted re...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2009-03, Vol.130 (3), p.295-300
Main Authors: Lu, Lei, Cao, Weiguo, Chen, Jie, Zhang, Hui, Zhang, Jiaping, Chen, Huiyun, Wei, Jiamei, Deng, Hongmei, Shao, Min
Format: Article
Language:English
Subjects:
1,3-Dipolar cycloaddition
Diastereoselectivity
Imidazoisoxazoles
Methyl 2-perfluoroalkynoates
Regioselectivity
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Summary:2-Perfluoroalkyl-3a,4,5,6-tetrahydroimidazo[1,5- b]isoxazoles 3 were obtained in good yields with high diastereoselectivity and regioselectivity via the reaction of excess methyl 2-perfluoroalkynoates 2 with cyclic nitrones 1 via 1,3-dipolar cycloaddition. ▪ Methyl 2-perfluoroalkynoates 2 reacted readily with cyclic nitrones 1 via 1,3-dipolar cycloaddition at room temperature to give 2-perfluoroalkyl-3a,4,5,6-tetrahydroimidazo[1,5- b]isoxazoles 3 in good to excellent yields with high diastereoselectivity and regioselectivity.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2008.11.002