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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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Supplementary files

Article information


Submitted
20 Jul 2007
Accepted
13 Aug 2007
First published
29 Aug 2007

Org. Biomol. Chem., 2007,5, 3190-3200
Article type
Paper

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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