Synthesis of Chiral 5-l-Menthyloxy-butyrolacto [3,4-d]isoxazoline Derivatives

Abstract

Abstract: The in situ regioselective 1,3-dipolar cycloaddition of substituted benzaldoxime to 5-(R)-(l-menthyloxy)-2(5H)-furanone using calcium hypochlorite as the oxidant waSInvestigated.Several substituted butyrolacto[3,4-d]isoxazoline compounds containing two novel stereogenic chiral centers were obtained.The structures of the target compounds have been established via the FAB-HRMS, NMR data(involved 1DNOESY) and X-ray diffraction analysis.The characteristic chemical shifts of the γ-lactone ring protonSIn¹HNMR were also discussed and the configurations of substituted phenyl furoisoxazolines, the adducts of benzonitrile oxide to 5-(R)-(l-menthyloxy)-2(5H)-furanone, could be determined unambiguously by analyzing the HNMR ata.

Key words: Chiral₅-l-menthyloxy-butyrolacto[3,4-d]isoxazoline, 1,3-Dipolar cycloaddition, Regioselective and stereoselective synthesis

CLC Number:

O621

TrendMD:

HUANG Hai-Hong, ZHANG Xiang, LIN Zi-Yun, CHEN Qing-Hua . Synthesis of Chiral 5-l-Menthyloxy-butyrolacto [3,4-d]isoxazoline Derivatives[J]. Chem. J. Chinese Universities, 2003, 24(11): 2000.

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Synthesis of Chiral 5-l-Menthyloxy-butyrolacto [3,4-d]isoxazoline Derivatives

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