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

页码：1308 / 1311

页数：4

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