Solution structures of a monodentate chiral lithium amide in the presence of lithium halide

Keizo Sugasawa, Mitsuru Shindo, Hiroshi Noguchi, Kenji Koga

Research output: Contribution to journalArticle

63 Citations (Scopus)

Abstract

Enantioselectivity of deprotonation reaction of 4-tert-butylcyclohexanone (2) by a monodentate chiral lithium amide ((R,R)-1) in THF is strongly influenced by the presence of lithium halides. Aggregation states of this chiral lithium amide in THF-d8 in the absence and in the presence of lithium halides were studied by 6Li and 15N NMR. It is concluded that the mixed dimer (D) is the species to give the high enantioselectivity of the reaction.

Original languageEnglish
Pages (from-to)7377-7380
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number41
DOIs
Publication statusPublished - Oct 7 1996
Externally publishedYes

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Lithium
Amides
Enantioselectivity
Deprotonation
Agglomeration
Nuclear magnetic resonance

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Solution structures of a monodentate chiral lithium amide in the presence of lithium halide. / Sugasawa, Keizo; Shindo, Mitsuru; Noguchi, Hiroshi; Koga, Kenji.

In: Tetrahedron Letters, Vol. 37, No. 41, 07.10.1996, p. 7377-7380.

Research output: Contribution to journalArticle

Sugasawa, Keizo ; Shindo, Mitsuru ; Noguchi, Hiroshi ; Koga, Kenji. / Solution structures of a monodentate chiral lithium amide in the presence of lithium halide. In: Tetrahedron Letters. 1996 ; Vol. 37, No. 41. pp. 7377-7380.
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