Organic Letters · 2004 · 151 citations · 27 references
Natural SciencesChemistryCatalysisOrganic ChemistryOrganometallic ChemistryCatalytic MechanismsOrganometallic SynthesisAlkylation CatalysisAllylic SubstitutionAsymmetric CatalysisEnantioselective SynthesisOrganoiridium ChemistryPhosphoramidite Chemistry
[reaction: see text] Linear or branched allylic carbonates or acetates undergo enantioselective iridium-catalyzed allylic substitution with sodium malonate. The reaction is wide in scope and affords the branched product in high yield and with high regio- (up to >99:1) and enantioselectivity (up to 98%). Ten aromatic or aliphatic substrates were successfully tested.
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Christoph Kiener, Chutian Shu, Christopher D. Incarvito et al. · Journal of the American Chemical Society · 2003 · 292 citations