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Issue 19, 2007
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Evaluating β-amino acids as enantioselective organocatalysts of the Hajos–Parrish–Eder–Sauer–Wiechert reaction

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Abstract

A systematic study of the effect of substitution within the β-amino acid framework indicates that both β2- and β3-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 β-amino acid (1R,2S)-cispentacin, which catalyses the Hajos–Parrish–Eder–Sauer–Wiechert reaction with comparable or higher levels of enantioselectivity to L-proline.

Graphical abstract: Evaluating β-amino acids as enantioselective organocatalysts of the Hajos–Parrish–Eder–Sauer–Wiechert reaction

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Publication details

The article was received on 20 Jul 2007, accepted on 13 Aug 2007 and first published on 29 Aug 2007


Article type: Paper
DOI: 10.1039/B711171A
Citation: Org. Biomol. Chem., 2007,5, 3190-3200
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    Evaluating β-amino acids as enantioselective organocatalysts of the Hajos–Parrish–Eder–Sauer–Wiechert reaction

    S. G. Davies, A. J. Russell, R. L. Sheppard, A. D. Smith and J. E. Thomson, Org. Biomol. Chem., 2007, 5, 3190
    DOI: 10.1039/B711171A

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