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Stereoselective Construction of α-Tetralone-Fused Spirooxindoles via Pd-Catalyzed Domino Carbene Migratory Insertion/Conjugate Addition Sequence
Organic Letters ( IF 5.2 ) Pub Date : 2017-09-22 00:00:00 , DOI: 10.1021/acs.orglett.7b02555
Dhanarajan Arunprasath 1 , Balasubramanian Devi Bala 1 , Govindasamy Sekar 1
Affiliation  

An efficient diastereoselective synthesis of α-tetralone-fused spirooxindoles is reported. The Pd-catalyzed domino reaction proceeds through a carbene migratory insertion followed by a 6-endo-trig mode of conjugate addition sequence from easily accessible isatin-derived N-tosylhydrazones and 2′-iodochalcones. The versatility of the protocol has been showcased by high functional group tolerance, broad substrate scope, and extension to an expedient synthesis of spiroacenaphthylenes. NMR reaction profiling and deuterium-labeling investigations provide insight into the mechanistic pathway.

中文翻译:

通过Pd催化的多米诺卡宾迁移插入/共轭加成序列立体选择性地构建α-四氢酮融合的螺恶唑

报道了一种有效的非对映选择性合成α-四氢萘酮融合的螺硫辛多酯的方法。通过卡宾洄游插入Pd催化的多米诺反应进行随后是6--三角函数从容易获得的靛红衍生的共轭加成序列的模式ñ -tosylhydrazones和2'- iodochalcones。高官能团耐受性,广泛的底物范围以及对螺iro烯的方便合成的扩展证明了该协议的多功能性。NMR反应谱分析和氘标记研究提供了有关机理途径的见解。
更新日期:2017-09-22
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