Regio- and stereoselective synthesis of isoxazolidine derivatives by asymmetric 1,3-dipolar cycloaddition reaction of chiral nitrones with 1-propene-1,3-sultone
Corresponding Author
Hong-Kui Zhang
Department of Chemistry, Xiamen University, Xiamen 361005, China
Department of Chemistry, Xiamen University, Xiamen 361005, ChinaSearch for more papers by this authorWing-Hong Chan
Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Hong Kong, China
Search for more papers by this authorAlbert W. M. Leeb
Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Hong Kong, China
Search for more papers by this authorWai-Yeung Wong
Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Hong Kong, China
Search for more papers by this authorCorresponding Author
Hong-Kui Zhang
Department of Chemistry, Xiamen University, Xiamen 361005, China
Department of Chemistry, Xiamen University, Xiamen 361005, ChinaSearch for more papers by this authorWing-Hong Chan
Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Hong Kong, China
Search for more papers by this authorAlbert W. M. Leeb
Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Hong Kong, China
Search for more papers by this authorWai-Yeung Wong
Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Hong Kong, China
Search for more papers by this authorAbstract
Asymmetric 1,3-dipolar cycloadditions of chiral nitrones to 1-propene-1,3-sultone (1) were investigated. Chiral nitrones 6a-e reacted with sultone 1 in toluene at 90 °C for 24-36 h to give the corresponding isoxazolidines in moderate yields with high regioselectivities and stereoselectivities. The diastereoselectivity of this reaction varied with the choice of dipolarophile and the steric demands of nitrones. When sultone 1 was allowed to react chiral nitrone 6e, a much better diastereoselectivity of up to 5.1:1 was observed.
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