Application of a metathesis reaction in the synthesis of sterically congested medium-sized rings. A direct ring closing versus a double bond migration–ring closing process?

Organic & Biomolecular Chemistry Pub Date: 2011-03-01 DOI: 10.1039/C1OB05086A

Abstract

An efficient double bond migration–ring closing metathesis reaction leading to cycloheptene derivatives is observed when specific sterically congested 1,9-dienes are treated with the Grubbs' imidazolidene ruthenium catalyst. The simultaneous use of the Grubbs' catalyst and RuClH(CO)(PPh3)3 facilitates the tandem bond migration–metathesis process. RuClH(CO)(PPh3)3 alone is capable of triggering an unactivated double bond migration that may have preparative applications.

Graphical abstract: Application of a metathesis reaction in the synthesis of sterically congested medium-sized rings. A direct ring closing versus a double bond migration–ring closing process
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