Organocatalytic Enantioselective 1,3-Dipolar Cycloadditions between Seyferth-Gilbert Reagent and Isatylidene Malononitriles: Synthesis of Chiral Spiro-phosphonylpyrazoline-oxindoles

被引：87
作者：
Du, Taiping [1 ]
Du, Fei [1 ]
Ning, Yanqiang [1 ]
Peng, Yungui [1 ]
机构：
[1] Southwest Univ, Key Lab Appl Chem Chongqing Municipal, Sch Chem & Chem Engn, Chongqing 400715, Peoples R China
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 05期
基金：
美国国家科学基金会;
关键词：
BESTMANN-OHIRA REAGENT; REGIOSELECTIVE SYNTHESIS; COMBINED NMR; EFFICIENT CONSTRUCTION; ASYMMETRIC-SYNTHESIS; PHOSPHINES SYNTHESIS; BIOLOGICAL-ACTIVITY; CINCHONA ALKALOIDS; DERIVATIVES; INHIBITORS;
D O I：
10.1021/acs.orglett.5b00311
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：1308 / 1311
页数：4
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