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2005
Aminocarboxylic acids (hydrazinocarboxylic acids) and esters
P 0270
Direct Organocatalytic Asymmetric Aldol Reactions of α-Amino Aldehydes:
Syntheses of Highly Enantiomerically Enriched anti-β-Hy02- 061 Expedient
droxy-α-amino Acids. — A simple and efficient method for the synthesis of highly
enantiomerically enriched title compounds is developed. L-Proline efficiently catalyzes
the reaction of a glycine aldehyde and affords anti-β-hydroxy-α-amino aldehydes with
high diastereoselectivity (dr up to >100:1). The latter are easily transformed into the
corresponding acid derivatives. Aldol reactions between (I) and -α-nonbranched aldehydes afford β-hydroxy-γ-amino aldehydes (X). — (THAYUMANAVAN, R.;
TANAKA*, F.; BARBAS, C. F. I.; Org. Lett. 6 (2004) 20, 3541-3544; Dep. Chem.,
Scripps Res. Inst., San Diego, La Jolla, CA 92037, USA; Eng.) — Steudel
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