Journal
TETRAHEDRON
Volume 69, Issue 26, Pages 5438-5443Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.04.103
Keywords
alpha-Amination; Organocatalysis; Amino Acids; Aspartic acid; Quaternary centers
Categories
Funding
- NSRF [PE 2431]
- ESF
- Greek State
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The enantioselective alpha-amination reaction of alpha,alpha-disubstituted aldehydes can lead to a variety of enantioenriched amino aldehydes, amino alcohols, and amino acids. After screening a variety of amino acids and their derivatives, we identified a cheap, simple, commercially available aspartic acid derivative that can catalyze efficiently the reaction between alpha,alpha-disubstituted aldehydes and dialkyl azodicarboxylates. The reaction proceeds smoothly leading to the corresponding alpha-aminated adducts in moderate to quantitative yields and moderate to high enantioselectivities (up to 96% ee). Finally, the conversion of these adducts to alpha,alpha-disubstituted quaternary amino acids is also described. 2013 Elsevier Ltd. All rights reserved.
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