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Angew Chem Int Ed Engl. 2015 Nov 09;54(46):13715-8. doi: 10.1002/anie.201506764. Epub 2015 Sep 17.

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

Angewandte Chemie (International ed. in English)

Dong Jin Lee, Donguk Ko, Eun Jeong Yoo

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). [email protected].

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.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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

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