The cycloaddition of nitrones with homochiral cyclopropanes.
The cycloaddition of nitrones and enantiomerically pure cyclopropane-1,1-dicarboxylates is examined. Transfer of optical activity to the adduct is dictated by thermal reaction conditions and nature of cyclopropane substitution. Optically active 2-substituted cyclopropane-1,1-dicarboxylates are shown to racemize under typical reaction conditions, providing evidence for a zwitterionic ring-opened intermediate.
Sapeta
Katarina
K
Department of Chemistry, The University of Western Ontario, London, Ontario, Canada N6A 5B7.
Kerr
Michael A
MA
D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D003521:Cyclopropanes; D009589:Nitrogen Oxides; C015388:nitrones