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Synthesis 1993; 1993(1): 62-64
DOI: 10.1055/s-1993-25794
short paper
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Synthese diastereomerenreiner α-Alkylamino-β-hydroxycarbonsäureester

Manfred Metzulat* , Gerhard Simchen
  • *Institut für Organische Chemie und Isotopenforschung der Universität Stuttgart, Pfaffenwaldring 55, D-7000 Stuttgart 80, Germany
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Publication Date:
17 September 2002 (online)

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Synthesis of Diastereomerically Pure α-Alkylamino-β-hydroxy-carboxylates By reaction of methyl [alkyl(trichloroacetyl)amino]acetates 1 with trimethylsilyl trifluoromethanesulfonate (2) the N-alkyl-N-[2-methoxy-2-trimethylsiloxy)vinyl]trichloroacetamides 3 are obtained. Aldol reaction of 3 with carbaldehydes 4 yields erythro/threo mixtures of 2-[alkyl(trichloroacetyl)amino]3-aryl-3-(trimethylsiloxy)propanoates 5. On treating the latter with methanolic hydrochloric acid pure erythro-2-(alkylamino)-3-aryl-3-hydroxypropanoates besides threo-2-[alkyl(trichloracetyl)amino]-3-aryl-3-hydroxypropanoates are prepared.