期刊
CHEMICAL COMMUNICATIONS
卷 57, 期 81, 页码 10576-10579出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1cc03240b
关键词
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资金
- National Natural Science Foundation of China [22171006, 21702003]
- Natural Science Foundation of Anhui Province [1808085QB31]
A palladium-catalysed construction of spiroindolines has been developed through dearomative spirocyclization of 3-(2-isocyanoethyl)indoles, yielding a variety of spiroindolines and bisheterocyclic compounds with high yields and enantioselectivity.
A palladium-catalysed construction of spiroindolines through dearomative spirocyclization of 3-(2-isocyanoethyl)indoles has been developed. 2 '-Aryl-, vinyl-, and alkyl-substituted spiroindolines could be accessed under mild conditions with excellent functional group tolerance. C1-tethered oxindole- and indole-spiroindoline bisheterocycles were generated in high yields via alkene/allene insertion and an imidoylative spirocyclization cascade. Additionally, a tandem dearomatization of two different indoles was realized with N-(2-bromobenzoyl)indoles as the electrophilic coupling partner of 3-(2-isocyanoethyl)indoles, affording polyindoline - spiroindoline bisheterocyclic scaffolds conveniently. Under the catalysis of Pd(OAc)(2) and a spinol-derived phosphoramidite ligand, chiral spiroindolines were successfully accessed with up to 95% yield and 85% ee.
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