Tetravinylethylene

Abstract

The first four-fold cross coupling reaction involving alkenic partners leads to the title hydrocarbon on multi-gram scale in one step from commercially available precursors. In stark contrast to its close structural relatives, tetravinylethylene is a remarkably robust, bench-stable compound. The π-bond rich hydrocarbon is shown to undergo one-pot sequences of pericyclic reactions leading to the formation of complex systems with four new rings, seven C-C bonds and ten stereocenters with a very high level of stereoselectivity. Insights into the reactivity of this and related systems is provided using the accurate composite ab initio MO G4(MP2) method. Targets very efficiently: The forgotten hydrocarbon, tetravinylethylene (TVE, scheme) is a bench-stable compound that can be synthesized in one step from commercially available starting materials. TVE is a vehicle for rapid complex molecule synthesis through one-pot sequences involving the stereoselective assembly of up to seven C-C bonds. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.