Journal of the American Chemical Society · 2010 · 320 citations · 19 references
Natural SciencesChemistryMedicinal ChemistryCatalysisSynthetic Medicinal ChemistryAmino Acid ChemistryCarboxylic AcidsCatalytic MechanismsAsymmetric CatalysisAsymmetric SynthesisCarboxylic Acid SynthesisChiral Carboxylic AcidsEnantioselective CatalysisEnantioselective Catalyst DesignEnantioselective SynthesisUnsaturated Carboxylic Acids
A novel amino-thiocarbamate-catalyzed bromolactonization of unsaturated carboxylic acids has been developed. The scope of the reaction is evidenced by 22 examples of γ-lactones with up to 99% yield and 93% ee. The protocol was applied in the enantioselective synthesis of the key intermediates of VLA-4 antagonists.
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Enantioselective Bromolactonization of Conjugated (<i>Z</i>)-Enynes
Wei Zhang, Suqing Zheng, Na Liu et al. · Journal of the American Chemical Society · 2010 · 349 citations
An Organocatalytic Asymmetric Chlorolactonization
Daniel C. Whitehead, Roozbeh Yousefi, Arvind Jaganathan et al. · Journal of the American Chemical Society · 2010 · 314 citations · Full text