Open AccessSynthesis of 1,5-dioxocanes via the two-fold C–O bond forming nucleophilic 4 + 4-cyclodimerization of cycloprop-2-en-1-ylmethanols
Author(s) -
Andrew Edwards,
Trevor Bennin,
Marina Rubina,
Michael Rubin
Publication year - 2015
Publication title -
rsc advances
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.746
H-Index - 148
ISSN - 2046-2069
DOI - 10.1039/c5ra14077c
Subject(s) - decane , chemistry , nucleophile , fold (higher order function) , stereochemistry , medicinal chemistry , organic chemistry , catalysis , mechanical engineering , engineering
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.
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