Stereochemistry of enantioselective deprotonation of 4-substituted cyclohexanones by chiral bidentate lithium amides

Masaharu Toriyama, Keizo Sugasawa, Mitsuru Shindo, Norio Tokutake, Kenji Koga

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Enantioselective deprotonation of 4-substituted cyclohexanones (1) in the presence of excess trimethylsilyl chloride was examined using chiral bidentate lithium amides ((R)-3~(R)-7 in THF. The solution structure of (R)-3a in THF in the presence and in the absence of lithium chloride were studied by NMR. It is concluded that the eight-membered cyclic transition state (10) offers reasonable explanation of the stereochemical course of the present reaction using (R)-3a.

Original languageEnglish
Pages (from-to)567-570
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number4
DOIs
Publication statusPublished - Jan 27 1997
Externally publishedYes

Fingerprint

Cyclohexanones
Lithium Chloride
Deprotonation
Stereochemistry
Lithium
Amides
Nuclear magnetic resonance
trimethylsilyl chloride

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Stereochemistry of enantioselective deprotonation of 4-substituted cyclohexanones by chiral bidentate lithium amides. / Toriyama, Masaharu; Sugasawa, Keizo; Shindo, Mitsuru; Tokutake, Norio; Koga, Kenji.

In: Tetrahedron Letters, Vol. 38, No. 4, 27.01.1997, p. 567-570.

Research output: Contribution to journalArticle

Toriyama, Masaharu ; Sugasawa, Keizo ; Shindo, Mitsuru ; Tokutake, Norio ; Koga, Kenji. / Stereochemistry of enantioselective deprotonation of 4-substituted cyclohexanones by chiral bidentate lithium amides. In: Tetrahedron Letters. 1997 ; Vol. 38, No. 4. pp. 567-570.
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