TY - JOUR
T1 - Highly enantioselective reduction with novel, bridged NADH models
AU - Kanomata, N.
AU - Nakata, T.
PY - 1997/1/1
Y1 - 1997/1/1
N2 - Biomimetic reduction of benzoylformate to mandelate with 97-99% ee was achieved with the diastereomeric, bridged NADH models (S.S)-1 and (R.S)-1. The oligomethylene bridge acts as an 'enzyme wall' and hinders the approach of the substrate from one side of the dihydropyridine ring. Isomers 1 were synthesized from the corresponding bridged nicotinate precursor, which was prepared by the reaction of formyl-substituted (vinylimino)phosphorane with methyl propiolate.
AB - Biomimetic reduction of benzoylformate to mandelate with 97-99% ee was achieved with the diastereomeric, bridged NADH models (S.S)-1 and (R.S)-1. The oligomethylene bridge acts as an 'enzyme wall' and hinders the approach of the substrate from one side of the dihydropyridine ring. Isomers 1 were synthesized from the corresponding bridged nicotinate precursor, which was prepared by the reaction of formyl-substituted (vinylimino)phosphorane with methyl propiolate.
KW - Asymmetric synthesis
KW - Macrocycles
KW - NADH model compounds
KW - Pyridinophanes
UR - http://www.scopus.com/inward/record.url?scp=0030739041&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0030739041&partnerID=8YFLogxK
U2 - 10.1002/anie.199712071
DO - 10.1002/anie.199712071
M3 - Article
AN - SCOPUS:0030739041
VL - 36
SP - 1207
EP - 1211
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 11
ER -