Enantiomerically pure alpha-amino aldehydes from silylated alpha-amino acids.
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 that < or =2% racemization occurs in the 1 --> 8 conversions.
Soto-Cairoli
Buddy
B
Department of Chemistry, University of Puerto Rico, Rio Piedras, Puerto Rico 00931-3346.
de Pomar
Jorge Justo
JJ
Soderquist
John A
JA
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D000596:Amino Acids; D017646:Organosilicon Compounds