1220632-49-4Relevant articles and documents
Synthesis of 3-methylenecyclohexan-1-ols by lewis acid catalyzed cyclization of (epoxy-allyl)silanes
Pulido, Francisco J.,Barbero, Asuncion,Castrenoa, Pilar
experimental part, p. 1307 - 1313 (2010/04/29)
A new route for the synthesis of (epoxy-allyl)silanes bearing the PhMe 2Si group has been developed and their acid-catalyzed cyclization studied. The so-called normal products derived from 5-exo or 6-endo attack were never obtained. On the contrary, an interesting tandem rearrangement/cyclization process was observed, which selectively led to 3-methylenecyclohexan-1-ols. A mechanism is proposed to explain this tandem reaction. The stereoselectivity of the cyclization process depends on the nature of the catalyst.