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

Kai-Lu Zheng; Wen-Ming Shu; Jun-Rui Ma; Yan-Dong Wu; An-Xin Wu

doi:10.1021/acs.orglett.6b01369

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

Org Lett. 2016 Aug 5;18(15):3526-9. doi: 10.1021/acs.orglett.6b01369. Epub 2016 Jul 11.

Authors

Kai-Lu Zheng¹, Wen-Ming Shu¹, Jun-Rui Ma¹, Yan-Dong Wu¹, An-Xin Wu^{1

2}

Affiliations

¹ Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University , Wuhan, Hubei 430079, P. R. China.
² State Key Laboratory of Applied Organic Chemistry, Lanzhou University , Lanzhou 730000, P. R. China.

PMID: 27396906
DOI: 10.1021/acs.orglett.6b01369

Abstract

A one-pot acid-mediated reaction has been developed for the N-H/α,β-C(sp(3))-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.

Publication types

Research Support, Non-U.S. Gov't