Abstract
Ring-opening metathesis and ring-closing metathesis (ROM-RCM) of bicyclo[4.2.0]octene-ynes and their application to the synthesis of tricyclic derivatives have been demonstrated using a second-generation ruthenium carbene complex. When bicycloalkene having a propargylamino group as an alkyne tether was reacted with a second-generation ruthenium carbene complex under an ethylene atmosphere, ROM-RCM proceeded to give tricyclic heterocycles in good yield. On the other hand, when the effect of the substituent on the alkyne was examined, cross metathesis (CM) of the alkyne part with ethylene proceeded to provide a conjugated diene derivative.
Highlights
Olefin metathesis contains a cleavage of carbon-carbon double bonds concomitantly with the formation of other ones by a metal carbene complex.[1]
The diene derivative is obtained by enyne metathesis, a twocarbon unit is thrown away as an ethylene by olefin metathesis
We recently developed Ring-opening metathesis and ring-closing metathesis (ROM-RCM) of cyclobutenylmethylamine 4 having an alkyne moiety in a tether catalyzed by second-generation Grubbs catalyst 1, and isoquinoline derivatives 5 could be obtained in good yields in a one-step reaction (Scheme 4).4d
Summary
Olefin metathesis contains a cleavage of carbon-carbon double bonds concomitantly with the formation of other ones by a metal carbene complex.[1].
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