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

✍ Scribed by Masaharu Toriyama; Keizo Sugasawa; Mitsuru Shindo; Norio Tokutake; Kenji Koga

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
188 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

Enantioselective deprotonation of 4-substituted cyclohexanones (1) in the presence of excess trimethylsilyl chloride was examined using chirai bidentate lithium amides ((R)-3~(R)-7) in THF. The solution structures 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.

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