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

Ying Xiao, Dawoon Jung, Tamara Gund, Sanjay V. Malhotra

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)681-686
Number of pages6
JournalJournal of Molecular Modeling
Volume12
Issue number5
DOIs
StatePublished - Jul 2006

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Computer Science Applications
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Computational Theory and Mathematics
  • Inorganic Chemistry

Keywords

  • B3LYP/6-31+G(3df,2p)
  • Chiral lithium amides
  • Cyclohexene oxide
  • Density functional activation energy
  • Enantioselective deprotonation
  • Theoretical study

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