Rhodium(II)-Catalyzed Cycloaddition Reactions of Non-classical 1,5-Dipoles for the Formation of Eight-Membered Heterocycles

Dong Jin Lee; Donguk Ko; Eun Jeong Yoo

doi:10.1002/anie.201506764

Rhodium(II)-Catalyzed Cycloaddition Reactions of Non-classical 1,5-Dipoles for the Formation of Eight-Membered Heterocycles

Angew Chem Int Ed Engl. 2015 Nov 9;54(46):13715-8. doi: 10.1002/anie.201506764. Epub 2015 Sep 17.

Authors

Dong Jin Lee¹, Donguk Ko¹, Eun Jeong Yoo²

Affiliations

¹ Department of Chemistry, Kangwon National University, 1 Kangwondaehak-gil, Chuncheon, 200-701 (Republic of Korea).
² Department of Chemistry, Kangwon National University, 1 Kangwondaehak-gil, Chuncheon, 200-701 (Republic of Korea). ejyoo@kangwon.ac.kr.

PMID: 26376924
DOI: 10.1002/anie.201506764

Abstract

A new type of intermolecular rhodium(II)-catalyzed [5+3] cycloaddition has been developed. This higher-order cycloaddition between pyridinium zwitterion 1,5-dipole equivalents and enol diazoacetates enables the formation of eight-membered heterocyclic skeletons, which are otherwise difficult to construct. The optimized cycloaddition occurs efficiently under mild conditions with a wide range of pyridinium zwitterions and with high functional-group tolerance.

Keywords: cycloaddition; eight-membered heterocycles; homogeneous catalysis; rhodium; zwitterions.