Journal of Zhejiang University SCIENCE
(ISSN 1009-3095, Monthly)

2005   Vol. 6B   No. 6   p.606-610

            [ Home Page ] | [ PDF Full Text ]   On-line Access Date:   May 22, 2005

Quantum chemical study on asymmetric allylation of benzaldehyde in the presence of chiral allylboronate

CHEN Wan-suo†, CHEN Zhi-rong

(Center of Unilab Chemical Engineering Reaction & Department of Chemical Engineering, Zhejiang University, Hangzhou 310027, China)
 †E-mail: wansuochen@yahoo.com.cn
Received Aug. 6, 2004; revision accepted Sept. 25, 2004

Abstract: 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.

Key words: Benzaldehyde, Asymmetric allylation, DFT
doi:10.1631/jzus.2005.B0606             CLC number: TQ150.9