title: Nucleophilic ring opening of cyclopropane hemimalonates using internal Brønsted acid activation.
abstract: The reaction of cyclopropanes, geminally disubstituted with one carboalkoxy and one carbohydroxy group, undergoes ring-opening reactions with indole nucleophiles under catalyst-free, hyperbaric (13 kbar) conditions. An internal hydrogen bond is postulated as the mode of activation obviating the need for the Lewis acid catalyst normally used for such donor-acceptor cyclopropane chemistry. These conditions avoid decarboxylation and yield useful adducts with the carboxylic acid group intact for further elaboration.
authors.affiliation: Department of Chemistry, The University of Western Ontario, London, Ontario, Canada N6A 5B7.
authors.forename: Michael R
authors.initials: MR
authors.lastname: Emmett
authors.forename: Michael A
authors.initials: MA
authors.lastname: Kerr
mesh_terms: D000143:Acids / Q000737:chemistry; D003521:Cyclopropanes / Q000737:chemistry*; D006860:Hydrogen Bonding; D008314:Malonates / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000143:Acids; D003521:Cyclopropanes; D008314:Malonates; C030797:cyclopropane