Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University , Chongqing 400715, P. R. China.
Org Lett. 2017 Nov 3;19(21):5806-5809. doi: 10.1021/acs.orglett.7b02763.
A methodology to access chiral 3,3'-spiro-phosphonylpyrazoline oxindoles via an asymmetric 1,3-dipolar cycloaddition reaction of substituted methyleneindolinones with α-diazomethylphosphonate in the catalysis of tertiary amine thiourea and 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) has been established. This method exhibits high functional group compatibility, where a wide range of methyleneindolinones with various substituents and heterocyclic rings are accommodated by this reaction. The resulting chiral 3,3'-spiro-phosphonylpyrazoline oxindoles can be further transformed into spiro-phosphonylcyclopropane oxindoles by ring contraction.
建立了一种通过取代亚甲基吲哚酮与α-重氮甲基膦酸酯在叔胺硫脲和 1,5-二氮杂双环[4.3.0]壬-5-烯(DBN)催化下的不对称 1,3-偶极环加成反应，来获得手性 3,3'-螺-磷酰基吡唑啉氧吲哚的方法。该方法具有很高的官能团兼容性，其中各种取代基和杂环的亚甲基吲哚酮都可以适应该反应。所得的手性 3,3'-螺-磷酰基吡唑啉氧吲哚可以通过环收缩进一步转化为螺-磷酰基环丙烷氧吲哚。
