(Chemical Equation Presented) Platinum dichloride-catalyzed hydroxy- or alkoxycyclization of cyclohexadienynes gives indenol derivatives, whereas hydroxy- or alkoxycyclization of cycloheptadienynes produces azulenol derivatives. The cyclization reaction proceeds via a cyclopropyl platinacarbene intermediate and allows for the direct stereocontrol of three contiguous stereogenic centers of the fused bicyclic skeletons. The transient reactive intermediate obtained from PtCl 2 -catalyzed cyclization reaction of a cyclohexadienyndiol can be trapped intramolecularly by a hydroxyl group to afford an oxatricyclo[18.104.22.168 4,8 ]-undecane ring skeleton with extreme diastereoselectivity.
ASJC Scopus subject areas
- Organic Chemistry