Enantioselective synthesis of fluorinated alpha-amino acids and derivatives in combination with ring-closing metathesis: intramolecular pi-stacking interactions as a source of stereocontrol |
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| Authors: | Fustero S Navarro A Pina B Soler J G Bartolomé A Asensio A Simón A Bravo P Fronza G Volonterio A Zanda M |
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| Affiliation: | Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Valencia, E-46100 Burjassot, Valencia, Spain. santos.fustero@uv.es |
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| Abstract: | [reaction: see text]. Hydride reduction of C=N bonds stereocontrolled by intramolecular pi-stacking interactions of 1-naphthylsulfinyl and N-aryl groups, nonoxidative Pummerer rearrangement, and ring-closing metathesis are efficiently combined in a highly stereoselective entry to enantiomerically pure cyclic and acyclic fluorinated beta-amino alcohols and alpha-amino acid derivatives, respectively. |
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