TY - JOUR
T1 - Stereoselective reduction of benzoin by the NADH model 3-(dimethylcarbamoyl)-1,2,4-trimethyl-1,4-dihydropyridine
AU - Beijer, N.A.
AU - Vekemans, J.A.J.M.
AU - Buck, H.M.
PY - 1990
Y1 - 1990
N2 - The Mg(ClO4)2-induced reduction of racemic benzoin by the racemic NADH model compound 3-(dimethylcarbamoyl)-1,2,4-trimethyl-1,4-dihydropyridine (1), in accordance to Cram's rule, leads exclusively to meso-1,2-diphenyl-1,2-ethanediol. However, while R-1 equally reduces 5-benzoin to afford meso-1,2-diphenyl-1,2-ethanediol, S-1 is reluctant to react with S-benzoin. The intermediacy of a strictly organized transition state, composed of chelated substrate, dihydropyridine and magnesium ion is involved.
AB - The Mg(ClO4)2-induced reduction of racemic benzoin by the racemic NADH model compound 3-(dimethylcarbamoyl)-1,2,4-trimethyl-1,4-dihydropyridine (1), in accordance to Cram's rule, leads exclusively to meso-1,2-diphenyl-1,2-ethanediol. However, while R-1 equally reduces 5-benzoin to afford meso-1,2-diphenyl-1,2-ethanediol, S-1 is reluctant to react with S-benzoin. The intermediacy of a strictly organized transition state, composed of chelated substrate, dihydropyridine and magnesium ion is involved.
U2 - 10.1002/recl.19901090708
DO - 10.1002/recl.19901090708
M3 - Article
SN - 0165-0513
VL - 109
SP - 434
EP - 436
JO - Recueil des Travaux Chimiques des Pays-Bas
JF - Recueil des Travaux Chimiques des Pays-Bas
IS - 7-8
ER -