Key Laboratory of Radiopharmaceuticals, College of Chemistry, Beijing Normal University, Beijing 100875, P. R. China.
Org Lett. 2015 Jul 2;17(13):3194-7. doi: 10.1021/acs.orglett.5b00826. Epub 2015 Jun 17.
1,3-Dipolar cycloadditions of triisopropylsilyl nitronates and 2-alkylacroleins produced isoxazolines bearing a chiral quaternary center in high yields and enantioselectivities with the aid of a chiral oxazaborolidine catalyst. One chiral isoxazoline product was converted to (R)-(+)-Tanikolide in 9 steps in a total yield of 43%.
三异丙基硅基硝酮与 2-烷基丙烯醛的 1,3-偶极环加成反应在手性恶唑硼烷催化剂的辅助下高产率、高对映选择性地得到了含有手性季碳中心的异恶唑啉。一个手性异恶唑啉产物经过 9 步反应,总收率为 43%,转化为(R)-(+)-Tanikolide。