Evaluating beta-amino acids as enantioselective organocatalysts of the Hajos-Parrish-Eder-Sauer-Wiechert reaction.
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.
Davies
Stephen G
SG
Department of Organic Chemistry, University of Oxford, Chemistry Research Laboratory, Oxford, UK. steve.davies@chem.ox.ac.uk
Russell
Angela J
AJ
Sheppard
Ruth L
RL
Smith
Andrew D
AD
Thomson
James E
JE
D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D008968:Molecular Conformation; D009277:Nandrolone / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000596:Amino Acids; D009277:Nandrolone