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The synthesis of a pseudo-tripeptide 9 and a pseudo-pentapeptide 1 incorporating the conformationally constrained β-amino acid (2S,3R)-2-amino cyclopropane carboxylic acid is reported. The key steps of the synthesis are the desymmetrisation of cyclopropane 1,2-dicarboxylic anhydride using (S)-proline t-butyl ester followed by a Curtius rearrangement. Subsequent trapping of the isocyanate with (S)-proline...
Stereoisomeric benzylidinemalonates have been synthesised. In the case of N-(2-ethoxycarbonyl-3-phenylpropenoyl)-2-oxazolidinone, both E- and Z-isomers could be obtained, but the Z-isomer isomerised (>95%) to the E-isomer in the presence of catalytic amounts of Rh(I) complex catalysts. For ethyl tertbutylamidobenzalmalonate, the Z-isomer initially predominates under Knoevenagel conditions, but...
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