RESUMEN

[reaction: see text]. Diastereoselective Strecker reactions based on (R)-phenylglycine amide as chiral auxiliary are reported. The Strecker reaction is accompanied by an in situ crystallization-induced asymmetric transformation, whereby one diastereomer selectively precipitates and can be isolated in 76-93% yield and dr > 99/1. The diastereomerically pure alpha-amino nitrile obtained from pivaldehyde (R1 = t-Bu, R2 = H) was converted in three steps to (S)-tert-leucine in 73% yield and >98% ee.

Asunto(s)

Amidas/química , Aminoácidos/síntesis química , Cristalización , Glicina/química , Cristalografía por Rayos X , Glicina/análogos & derivados , Espectroscopía de Resonancia Magnética , Modelos Químicos , Modelos Moleculares , Estereoisomerismo , Temperatura