Acid-Mediated N–H/α,β-C(sp3)–H Trifunctionalization of Pyrrolidine: Intermolecular [3 + 2] Cycloaddition for the Construction of 2,3-Dihydro‑1H‑Pyrrolizine Derivatives

A one-pot acid-mediated reaction has been developed for the N–H/α,β-C­(sp3)–H trifunctionalization of pyrrolidine without any metallic reagents or external oxidants. This reaction involves the intermolecular [3 + 2] cycloaddition of in situ-generated azomethine ylides with acrylic esters to provide...

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Bibliographic Details
Published in:Organic letters 2016-08, Vol.18 (15), p.3526-3529
Main Authors: Zheng, Kai-Lu, Shu, Wen-Ming, Ma, Jun-Rui, Wu, Yan-Dong, Wu, An-Xin
Format: Article
Language:English
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Summary:A one-pot acid-mediated reaction has been developed for the N–H/α,β-C­(sp3)–H trifunctionalization of pyrrolidine without any metallic reagents or external oxidants. This reaction involves the intermolecular [3 + 2] cycloaddition of in situ-generated azomethine ylides with acrylic esters to provide facile access to 2,3-dihydro-1H-pyrrolizine derivatives in high yields under mild conditions.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b01369