Enantiomerically Pure α-Amino Aldehydes from Silylated α-Amino Acids
Autor: | Buddy Soto-Cairoli, John A. Soderquist, Jorge C. Justo de Pomar |
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Rok vydání: | 2007 |
Předmět: |
chemistry.chemical_classification
Aldehydes Molecular Structure Stereochemistry Chemistry Organic Chemistry Molecular Conformation Stereoisomerism Crystallography X-Ray Biochemistry Article Amino acid Hydrolysis Organic chemistry Organosilicon Compounds Amino Acids Physical and Theoretical Chemistry Racemization |
Zdroj: | Organic Letters. 10:333-336 |
ISSN: | 1523-7052 1523-7060 |
DOI: | 10.1021/ol7028993 |
Popis: | The disilylation of alpha-amino acids 1 to provide 2 (72-87%) was achieved without racemization. An unprecedented borane-mediated semi-reduction strategy was devised to convert 2 to stable, isolable oxazaborolidines 3 (100%) which were hydrolyzed to provide 5 (49-60%) as pure, stable compounds. Analysis of the Mosher amides (8) of the gamma-amino esters 7 reveals thator =2% racemization occurs in the 1 --8 conversions. |
Databáze: | OpenAIRE |
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