Organocatalytic Enantioselective 1,3-Dipolar Cycloadditionsbetween Seyferth−Gilbert Reagent and Isatylidene Malononitriles:Synthesis of Chiral Spiro-phosphonylpyrazoline-oxindoles
Organocatalytic Enantioselective 1,3-Dipolar Cycloadditionsbetween Seyferth−Gilbert Reagent and Isatylidene Malononitriles:Synthesis of Chiral Spiro-phosphonylpyrazoline-oxindoles
复制标题
Seyferth-Gilbert 试剂与异亚替丁丙二腈之间的有机催化对映选择性 1,3-偶极环加成：手性螺磷酰基吡唑啉-羟吲哚的合成
DOI：
10.1021/acs.orglett.5b00311
复制
发表时间：
2015
期刊：
影响因子：
--
通讯作者：
Yungui Peng
中科院分区：
文献类型：
--
作者：
Taiping Du;Fei Du;Yanqiang Ning;Yungui Peng
以金鸡纳生物碱衍生物为催化剂，研究了Seyferth-Gilbert试剂（SGR）与异亚甲基丙二腈的1，3-偶极环加成反应.该方法以良好的产率和对映选择性合成了一系列手性螺膦酰基吡唑啉-羟吲哚。该方法的合成效用进一步证明了其使用的三组分多米诺反应，涉及靛红，丙二腈，和SGR的基础上连续Knoevenagel缩合和1，3-偶极环加成反应。
A new method has been developed for the catalytic enantioselective 1,3-dipolar cycloaddition of the Seyferth–Gilbert reagent (SGR) to isatylidene malononitriles using a cinchona alkaloid derivative as a catalyst. This method allowed for the synthesis of a series of chiral spiro-phosphonylpyrazoline-oxindoles in good yields with excellent enantioselectivities. The synthetic utility of this method was further demonstrated by its use in a three-component domino reaction involving isatin, malononitrile, and SGR based on sequential Knoevenagel condensation and 1,3-dipolar cycloaddition reactions.