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. 2008 Jan 17;10(2):333-6.
doi: 10.1021/ol7028993. Epub 2007 Dec 20.

Enantiomerically pure alpha-amino aldehydes from silylated alpha-amino acids

Buddy Soto-Cairoli  1 , Jorge Justo de Pomar, John A Soderquist
Affiliations

Enantiomerically pure alpha-amino aldehydes from silylated alpha-amino acids

Buddy Soto-Cairoli et al. Org Lett. .

Abstract

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.

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Figures

Figure 1
Figure 1
Space-filling MM model of phenylglycinal 5g.
Figure 2
Figure 2
X-Ray structure of the Mosher amide 8a
Scheme 1
Scheme 1
Scheme 2
Scheme 2
See this image and copyright information in PMC

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