Synthesis of 1,5-dioxocanes via the two-fold C-O bond forming nucleophilic 4 + 4-cyclodimerization of cycloprop-2-en-1-ylmethanolsElectronic supplementary information (ESI) available: Experimental details. CCDC 1408273. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5ra14077c

An efficient [4 + 4] cyclodimerization of cyclopropenemethanols operating via a two-fold strain release-driven addition of alkoxides across the double bond of cyclopropenes was investigated. This chemo- and diastereoselective transformation provided previously unknown 2,7-dioxatricyclo[7.1.0.0 4,6 ]decane scaffolds. An efficient chemo- and diastereoselective 4 + 4 cyclodimerization of cyclopropenemethanols provided previously unknown 2,7-dioxatricyclo[7.1.0.0 4,6 ]decane scaffolds.