Effect of ring size on the exo/endo selectivity of a thermal double cycloaddition of fused pyran-2-ones

Kristof Kranjc; Franc Perdih; Marijan Kocevar

doi:10.1021/jo9011199

Effect of ring size on the exo/endo selectivity of a thermal double cycloaddition of fused pyran-2-ones

J Org Chem. 2009 Aug 21;74(16):6303-6. doi: 10.1021/jo9011199.

Authors

Kristof Kranjc¹, Franc Perdih, Marijan Kocevar

Affiliation

¹ Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, SI-1000 Ljubljana, Slovenia. kristof.kranjc@fkkt.uni-lj.si

PMID: 19572585
DOI: 10.1021/jo9011199

Abstract

A study of an unusual effect of the size of the ring fused to 2H-pyran-2-ones on the exo/endo selectivity of a thermal double cycloaddition of N-substituted maleimides or maleic anhydride yielding bicyclo[2.2.2]octene derivatives is presented. With subtle variations of starting compounds and reaction conditions exclusively exo,exo or exo,endo products can be prepared.