On the scope of asymmetric nitrile oxide cycloadditions with Oppolzer's chiral sultam. Total syntheses of (+)-hepialone,(-)-(1R, 3R, 5S)-1, 3-dimethyl-2, 9-dioxabicyclo [ …
DP Curran, TA Heffner
文献索引：Curran, Dennis P.; Heffner, Timothy A. Journal of Organic Chemistry, 1990 , vol. 55, # 15 p. 4585 - 4595
Cycloadditions of nitrile oxides with acryloyl derivatives of Oppolzer's chiral sultam produce stereoisomeric A2-isoxazolines in ratios of about 90/10 at 25" C. The major diastereomers can be isolated in pure form in 7043% yield. Syntheses of the three title natural products are used to illustrate that optically pure isoxazolines can be transformed into a wide variety of functional groups including@, y-dihydroxy ketones, alcohols, 1, 2-and 1, 3-diols, 1, 3, 4- ...
