Enantioselective Construction of Dihydropyrido[1,2‑a]indoles via Organocatalytic Arylmethylation of 2‑Enals with Inert Aryl Methane Nucleophiles

An organocatalytic asymmetric arylmethylation/N-hemiacetalization of 2-indolyl methane derivatives and 2-enals was developed. Notably, the 2-methyl of indole was readily deprotonated to produce highly reactive nucleophilic species by introducing the nitro group at the C3 position of the indole ring....

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Bibliographic Details
Published in:Organic letters 2019-07, Vol.21 (14), p.5514-5518
Main Authors: Ding, Xiang-Feng, Yang, Wu-Lin, Mao, Jia, Cao, Cong-Xian, Deng, Wei-Ping
Format: Article
Language:English
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Summary:An organocatalytic asymmetric arylmethylation/N-hemiacetalization of 2-indolyl methane derivatives and 2-enals was developed. Notably, the 2-methyl of indole was readily deprotonated to produce highly reactive nucleophilic species by introducing the nitro group at the C3 position of the indole ring. A spectrum of valuable chiral dihydropyrido­[1,2-a]­indoles were efficiently constructed with excellent enantioselectivity (up to >99% ee). Furthermore, the corresponding products could be easily functionalized via simple deprotonation and treatment with other electrophiles with excellent diastereoselectivities (>20:1 dr).
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b01837