An experimental and theoretical study of the enantioselective deprotonation of cyclohexene oxide with isopinocampheyl-based chiral lithium amides

Document Type

Article

Publication Date

7-1-2006

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. © Springer-Verlag 2006.

Identifier

33746421024 (Scopus)

Publication Title

Journal of Molecular Modeling

External Full Text Location

https://doi.org/10.1007/s00894-006-0114-2

e-ISSN

09485023

ISSN

16102940

PubMed ID

16705421

First Page

681

Last Page

686

Issue

5

Volume

12

Grant

9750809

Fund Ref

National Science Foundation

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