Redox-Triggered α‑C–H Functionalization of Pyrrolidines: Synthesis of Unsymmetrically 2,5-Disubstituted Pyrrolidines

Redox-Triggered α‑C–H Functionalization of Pyrrolidines: Synthesis of Unsymmetrically 2,5-Disubstituted Pyrrolidines

By using o-benzoquinone as an internal oxidant, the regio- and diastereoselective functionalization of the secondary over the tertiary α-C–H bond of 2-substituted pyrrolidines is first realized. Subsequent intermolecular addition of a nucleophile to the generated N,O-acetal and cleavage of the aroma...

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Veröffentlicht in:Organic letters 2015-10, Vol.17 (19), p.4758-4761
Hauptverfasser: Cheng, Yong-Feng, Rong, Hao-Jie, Yi, Cheng-Bo, Yao, Jun-Jun, Qu, Jin
Format: Artikel
Sprache:eng
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Zusammenfassung:By using o-benzoquinone as an internal oxidant, the regio- and diastereoselective functionalization of the secondary over the tertiary α-C–H bond of 2-substituted pyrrolidines is first realized. Subsequent intermolecular addition of a nucleophile to the generated N,O-acetal and cleavage of the aromatic substituent leads to 2,5-disubstituted pyrrolidines.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02298