Enantiomerically Pure α-Amino Aldehydes from Silylated α-Amino Acids

Autor: Buddy Soto-Cairoli, John A. Soderquist, Jorge C. Justo de Pomar
Rok vydání: 2007
Předmět:
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