Dynamic Kinetic Resolution in the Asymmetric Synthesis of β-Amino Acids by Organocatalytic Reduction of Enamines with Trichlorosilane

Resolved dynamically: A new, expedient protocol has been developed for the asymmetric synthesis of β3‐ and β2, 3‐amino acid derivatives from enamine precursors (see scheme). The method relies on a fast equilibrium between the enamine and imine forms. Reduction of the imine with Cl3SiH, catalyzed by...

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Bibliographic Details
Published in:Chemistry : a European journal 2008-09, Vol.14 (27), p.8082-8085
Main Authors: Malkov, Andrei V., Stončius, Sigitas, Vranková, Kvetoslava, Arndt, Matthias, Kočovský, Pavel
Format: Article
Language:English
Subjects:
Amides - chemistry
Amines - chemical synthesis
Amines - chemistry
amino acids
Amino Acids - chemical synthesis
Amino Acids - chemistry
asymmetric synthesis
Catalysis
Hydrogen-Ion Concentration
imines
Kinetics
Molecular Structure
organocatalysis
Oxidation-Reduction
reduction
Silanes - chemistry
Stereoisomerism
Thermodynamics
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Summary:Resolved dynamically: A new, expedient protocol has been developed for the asymmetric synthesis of β3‐ and β2, 3‐amino acid derivatives from enamine precursors (see scheme). The method relies on a fast equilibrium between the enamine and imine forms. Reduction of the imine with Cl3SiH, catalyzed by the L‐valine‐derived formamide L* (5 mol %), afforded the corresponding amino esters in good yields, good enantioselectivities (≤90 % ee) and high diastereoselectivities (≤99 % de).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.200801244