Quantum chemical study on asymmetric allylation of benzaldehyde in the presence of chiral allylboronate.
The quantum chemical method is employed to study the modified asymmetric allylation of benzaldehyde controlled by diisopropyl D-(-)-tartrate auxiliary. All the structures are optimized completely at the B3LYP/6-31G(d,p) level. The (R)-secondary alcohol can be achieved mainly through a six-membered ring chair-like transition state structure. From the relative reaction rates theory the main product configuration predicted is in agreement with the experiment result.
Chen
Wan-suo
WS
Center of Unilab Chemical Engineering Reaction & Department of Chemical Engineering, Zhejiang University, Hangzhou 310027, China. wansuochen@yahoo.com.cn
Chen
Zhi-rong
ZR
D001547:Benzaldehydes / Q000032:analysis / Q000737:chemistry*; D001897:Boronic Acids / Q000032:analysis / Q000737:chemistry*; D002244:Carbon / Q000032:analysis / Q000737:chemistry; D003198:Computer Simulation; D006859:Hydrogen / Q000032:analysis / Q000737:chemistry; D007536:Isomerism; D008956:Models, Chemical; D008958:Models, Molecular; D008968:Molecular Conformation; D044367:Phase Transition; D011789:Quantum Theory; D012996:Solutions
D001547:Benzaldehydes; D001897:Boronic Acids; D012996:Solutions; D002244:Carbon; D006859:Hydrogen; C032175:benzaldehyde