Organic Letters · 2003 · 26 citations · 16 references
Natural SciencesChemistryCatalysisOrganic ChemistryOrganometallic ChemistryCatalytic MechanismsHeterocyclic ChemistryMolecular Orbital TheoryReaction MechanismsAlkylation ProcessesAlkylation ReactionsAsymmetric CatalysisDouble Bond ConfigurationEnantioselective CatalysisEnantioselective Synthesis
[reaction: see text] The first alkylative and enantioselective ring-opening of COT-monoepoxide (1) without the occurrence of any ring-contraction-isomerization by the use of in situ-formed organocuprates is reported. Because of the particular geometric constraint of compound 1, this work reports the largest deviation from coplanarity between the pi-orbital of the double bond and the sigma-bond connecting the leaving group ever observed for an S(N)2'-cuprate alkylation.
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