A highly reusable rhodium catalyst-organic framework for the intramolecular cycloisomerization of 1,6-enynes

Elizabeth G Corkum; Michael J Hass; Andrew D Sullivan; Steven H Bergens

doi:10.1021/ol201333s

A highly reusable rhodium catalyst-organic framework for the intramolecular cycloisomerization of 1,6-enynes

Org Lett. 2011 Jul 1;13(13):3522-5. doi: 10.1021/ol201333s. Epub 2011 May 31.

Authors

Elizabeth G Corkum¹, Michael J Hass, Andrew D Sullivan, Steven H Bergens

Affiliation

¹ Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada T6G 2G2.

PMID: 21627077
DOI: 10.1021/ol201333s

Abstract

The intramolecular cycloisomerization of 1,6-enynes in 95-99% ee is reported using an immobilized Rh catalyst-organic framework synthesized from alternating ring-opening metathesis polymerization (altROMP) assembly. The framework was reused up to seven times, and it was used in high turnover number (TON) batch reactions. The catalyst provided the highest TONs to date (up to 890) for the cycloisomerizations, with catalyst loadings ranging from 0.2 to 0.06 mol %.