- Diastereoselective formation of (Z)-didehydroamino acid esters
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The rearrangement of (E)-didehydroamino acid derivatives to the corresponding Z-derivatives under acid or basic catalysis as well as under the influence of radicals has been investigated. The condensation of N-benzyloxycarbonyl or N-tert-butoxycarbonyl protected alkyl 2-amino-2-(dimethoxyphosphoryl)acetates with aldehydes or ketones in dichloromethane in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene furnishes (Z)-didehydroamino acid ester derivatives diastereoselectively in excellent yields and with high purity.
- Schmidt,Griesser,Leitenberger,Lieberknecht,Mangold,Meyer,Riedl
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p. 487 - 490
(2007/10/02)
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- Amino acids and peptides; 75. Synthesis of di- and trihydroxyamino acids - Construction of lipophilic tripalmitoyldihydroxy-α-amino acids
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Suitable protected derivatives of trihydroxynorleucines-[(2S,4S,5S)- and (2R,4S,5S)-2-amino-4,5,6-trihydroxyhexanoic acid], of all isomeric dihydroxynorvalines [2-amino-4,5-dihydroxypentanoic acids), of all isomeric 2-amino-6,7-dihydroxyheptanoic acids an
- Schmidt,Lieberknecht,Kazmaier,Griesser,Jung,Metzger
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