An experimental and theoretical study of the enantioselective deprotonation of cyclohexene oxide with isopinocampheyl-based chiral lithium amides |
| |
Authors: | Ying Xiao Dawoon Jung Tamara Gund Sanjay V Malhotra |
| |
Institution: | (1) Department of Chemistry and Environmental Science, New Jersey Institute of Technology, University Heights, Newark, NJ 07102, USA |
| |
Abstract: | The mechanism of the enantioselective deprotonation of cyclohexene oxide with isopinocampheyl-based chiral lithium amide was studied by quantum chemical calculations. The transition states of eight molecules were fully optimized at the ab initio HF/3-21G and density functional B3LYP/3-21G levels with Gaussian 98. The activation energies were calculated at the B3LYP/6-31+G(3df,2p)//B3LYP/3-21G level. We found the theoretical evaluation to be consistent with the experimental data. At the best case, an enantiomeric excess of up to 95% for (R)-2-scyclohexen-1-ol was achieved with (−)-N, N-diisopinocampheyl lithium amide.
Enantioselective deprotonation of cyclohexene oxide
Electronic Supplementary Material Supplementary material is available for this article at
Dedicated to Professor Dr. Paul von Ragué Schleyer on the occasion of his 75th birthday. |
| |
Keywords: | Theoretical study Enantioselective deprotonation Cyclohexene oxide Chiral lithium amides Density functional activation energy B3LYP/6-31+G(3df 2p) |
本文献已被 PubMed SpringerLink 等数据库收录! |