《1,3-Dipolar Cycloaddition of Substituted Benzonitrile Oxide to 5-(R)-(l-Menthyloxy)-2(5H)-furanone》.pdfVIP

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《1,3-Dipolar Cycloaddition of Substituted Benzonitrile Oxide to 5-(R)-(l-Menthyloxy)-2(5H)-furanone》.pdf

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《1,3-Dipolar Cycloaddition of Substituted Benzonitrile Oxide to 5-(R)-(l-Menthyloxy)-2(5H)-furanone》.pdf

Chinese Chemical Letters Vol. 13, No. 7, pp 593 – 596, 2002 593 /journal/ccl/html 1,3-Dipolar Cycloaddition of Substituted Benzonitrile Oxide to 5-(R)- (l-Menthyloxy)-2(5H)-furanone 1 1 2 Hai Hong HUANG , Xiang ZHANG *, Qing Hua CHEN 1Institute of Materia Medica, Chinese Academy of Medical Sciences Peking Union Medical College, Beijing 100050 2Department of Chemistry, Beijing Normal University, Beijing 100875 Abstract: Several isoxazoline compounds were obtained by the 1,3-dipolar cycloaddition of benzonitrile oxide to 5-(R)-(l-menthyloxy)-2(5H)-furanone . The reaction condition was investigated preliminarily, the structures of these compounds have been established via the analysis of NMR data(involved NOEID or HMBC) and the reaction seems occurred regioselectively. 1 Keywords: 1,3-Dipolar cycloaddition, benzonitrile oxide, c onfiguration , H-NMR, NOE. Isoxazoline compounds as key intermediates for construction of natural products have been developed very fast as an hot area in organic synthesis 1. 5-(R)-(l-menthyloxy)- 2(5H)- furanone as a valuable chiral synthon has been recently studied for its high 2