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

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

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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
Issue number4
Publication statusPublished - Jan 27 1997
Externally publishedYes


All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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