Tandem RCM-Claisen Rearrangement-[2+2] cycloaddition of O,O'-(But-2-en-1,4-diyl)-bridged binaphthols

Abstract

Attempted RCM of 2,2'-bis(allyloxy)-1,1'-binaphthyl resulted in a Claisen-type rearrangement of a postulated labile dioxacyclodecine proceeding at room temperature and followed by [2+2] cycloaddition. Structures of products were confirmed by X-ray crystallography. A mechanistic rationalisation based on relative stabilities of proposed intermediates and transition states is provided. © 2012 by the authors; licensee MDPI, Basel, Switzerland.