Synthesis of Chiral, Non-racemic Aldols from Chiral β-Hydroxy-Weinreb Amides Prepared by Enantioselective Reformatsky-like Reaction Induced by Chiral β-Aminoalcohols

Chiral 1,2-aminoalcohols catalyze enantioselective Reformatsky addition of zinc derivatives of α-bromo Weinreb amides. Reaction of Grignard reagents with the resulting β-hydroxy N-methoxy- N-methyl amides allowed the preparation of β-hydroxy ketones regio- and enantioselectively.

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Bibliographic Details
Published in:Tetrahedron 2000-02, Vol.56 (9), p.1217-1223
Main Authors: Andrés, José M, Pedrosa, Rafael, Pérez-Encabo, Alfonso
Format: Article
Language:English
Subjects:
chiral aminoalcohols
enantioselective synthesis
Reformatsky reaction
stereoselective aldol reaction
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Description
Summary:Chiral 1,2-aminoalcohols catalyze enantioselective Reformatsky addition of zinc derivatives of α-bromo Weinreb amides. Reaction of Grignard reagents with the resulting β-hydroxy N-methoxy- N-methyl amides allowed the preparation of β-hydroxy ketones regio- and enantioselectively.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(99)01070-4