A Unified Catalytic Asymmetric (4+1) and (5+1) Annulation Strategy to Access Chiral Spirooxindole‐Fused Oxacycles

Autor:	Qianlan Xu, Min Gao, Xiangnan Gong, Yuanzhi Xia, Lin Hu, Yukun Zhao, Yanshu Luo
Rok vydání:	2021
Předmět:	chemistry.chemical_compound Annulation chemistry Nucleophile Organocatalysis Synthon General Chemistry General Medicine Bifunctional Combinatorial chemistry Catalysis Umpolung
Zdroj:	Angewandte Chemie. 133:19966-19973
ISSN:	1521-3757 0044-8249
DOI:	10.1002/ange.202105282
Popis:	A unified catalytic asymmetric (N+1) (N=4, 5) annulation reaction of oxindoles with bifunctional peroxides has been achieved in the presence of a chiral phase-transfer catalyst (PTC). This general strategy utilizes peroxides as unique bielectrophilic four- or five-atom synthons to participate in the C-C and the subsequent umpolung C-O bond-forming reactions with one-carbon unit nucleophiles, thus providing a distinct method to access the valuable chiral spirooxindole-tetrahydrofurans and -tetrahydropyrans with good yields and high enantioselectivities under mild conditions. DFT calculations were performed to rationalize the origin of high enantioselectivity. The gram-scale syntheses and synthetic utility of the resultant products were also demonstrated.
Databáze:	OpenAIRE
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