By rational design, novel atropisomeric 1,1-binaphthylazepine-based 1,2-amino alcohols 1f and 1g have been prepared in enantiopure form and tested as catalytic precursors in the enantioselective addition of diethylzinc to aromatic aldehydes: the corresponding (S)-1-arylpropanols have been obtained in quantitative yields and e.e.s up to 95%. A rationale explaining the stereochemical outcome of the reaction, as well as the influence of structural features of the ligands on the enantioselectivity of the addition, is also provided.

Rational Design of Chiral 1,1’-Binaphthylazepine-based Ligands for the Enantioselective Addition of ZnEt2 to Aromatic Aldehydes

SUPERCHI, Stefano;SCAFATO, Patrizia;ROSINI, Carlo
2002-01-01

Abstract

By rational design, novel atropisomeric 1,1-binaphthylazepine-based 1,2-amino alcohols 1f and 1g have been prepared in enantiopure form and tested as catalytic precursors in the enantioselective addition of diethylzinc to aromatic aldehydes: the corresponding (S)-1-arylpropanols have been obtained in quantitative yields and e.e.s up to 95%. A rationale explaining the stereochemical outcome of the reaction, as well as the influence of structural features of the ligands on the enantioselectivity of the addition, is also provided.
2002
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11563/17655
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