Asymmetric hydroformylation of vinyl acetate: application in the synthesis of optically active isoxazolines and imidazoles.
(R)- and (S)-2-(Acetyloxy)-propanal were prepared [93.8% ee, 102 b/l for (R), 96.9% ee, 149 b/l for (S)] via asymmetric hydroformylation of vinyl acetate on a 150-180 g scale and were used as the starting materials in the synthesis of chiral isoxazoline and imidazole derivatives which proceeded without racemization of the chiral center.
Thomas
P J
PJ
Corporate R&D, The Dow Chemical Company, 1776 Building, Midland, MI 48674, USA. pjthomas@dow.com
Axtell
Alex T
AT
Klosin
Jerzy
J
Peng
Wei
W
Rand
Cynthia L
CL
Clark
Thomas P
TP
Landis
Clark R
CR
Abboud
Khalil A
KA
D018360:Crystallography, X-Ray; D007093:Imidazoles / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007555:Isoxazoles / Q000138:chemical synthesis*; D008958:Models, Molecular; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
D007093:Imidazoles; D007202:Indicators and Reagents; D007555:Isoxazoles; D014753:Vinyl Compounds; C011566:vinyl acetate