The beta-amino acid cispentacin promotes the Hajos-Parrish-Eder-Sauer-Wiechert reaction with levels of enantioselectivity comparable to or higher than proline.
A systematic study of the effect of substitution within the beta-amino acid framework indicates that both beta(2)- and beta(3)-amino acids catalyse the Hajos-Parrish-Eder-Sauer-Wiechert reaction with poor to reasonable levels of enantioselectivity. These results led to the evaluation of the conformationally constrained beta-amino acid (1R,2S)-cispentacin, which catalyses the Hajos-Parrish-Eder-Sauer-Wiechert reaction with comparable or higher levels of enantioselectivity to L-proline.
An enantioselective hydrogenation of hydrazones catalyzed by Rh complexes (Rh-Josiphos or Rh-Taniaphos) has been developed. The protocol can be applied to hydrazones with three different protective groups (Boc, Cbz, and methoxycarbonyl), allowing for selective deprotection and further elaboration of the hydrazine products in the presence of other functional groups.
Enantioselective syntheses O 0031Highly Enantioselective Organocatalysis of the Hajos-Parrish-Eder-Sauer-Wiechert Reaction by the β-Amino Acid Cispentacin. -The β-amino acid cispentacin promotes the title reaction with levels of enantioselectivity comparable to or higher than those of proline. -(DAVIES*, S. G.; SHEPPARD, R. L.; SMITH, A. D.; THOMSON, J. E.; Chem. Commun. (Cambridge) 2005, 30, 3802-3804; Chem. Res. Lab., Dep. Chem., Univ. Oxford, Oxford OX1 3TA, UK; Eng.) -M. Paetzel 50-030
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