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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.

Original publication

DOI

10.1039/b711171a

Type

Journal article

Journal

Org Biomol Chem

Publication Date

07/10/2007

Volume

5

Pages

3190 - 3200

Keywords

Amino Acids, Catalysis, Molecular Conformation, Nandrolone, Stereoisomerism