Organocatalytic enantioselective 1,3-dipolar cycloadditions between Seyferth-Gilbert reagent and isatylidene malononitriles: synthesis of chiral spiro-phosphonylpyrazoline-oxindoles.
作者： Taiping Du , Fei Du , Yanqiang Ning , Yungui Peng
DOI: 10.1021/ACS.ORGLETT.5B00311
关键词: Enantioselective synthesis 、 Isatin 、 Organic chemistry 、 Cycloaddition 、 Reagent 、 Cinchona 、 Knoevenagel condensation 、 Chemistry 、 Cascade reaction 、 Malononitrile
摘要: A new method has been developed for the catalytic enantioselective 1,3-dipolar cycloaddition of Seyferth–Gilbert reagent (SGR) to isatylidene malononitriles using a cinchona alkaloid derivative as catalyst. This allowed synthesis series chiral spiro-phosphonylpyrazoline-oxindoles in good yields with excellent enantioselectivities. The synthetic utility this was further demonstrated by its use three-component domino reaction involving isatin, malononitrile, and SGR based on sequential Knoevenagel condensation reactions.
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