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

Autor:	Mitsuru Shindo, Kenji Koga, Masaharu Toriyama, Norio Tokutake, Keizo Sugasawa
Rok vydání:	1997
Předmět:	Trimethylsilyl chloride Denticity Stereochemistry Organic Chemistry Enantioselective synthesis chemistry.chemical_element Biochemistry Solution structure chemistry.chemical_compound Deprotonation chemistry Drug Discovery Lithium chloride Lithium
Zdroj:	Tetrahedron Letters. 38:567-570
ISSN:	0040-4039
Popis:	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 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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::306f3835aab0a51787ad23ee00248cc6 https://doi.org/10.1016/s0040-4039(96)02373-8 Zobrazit plný text záznamu Full Text from ScienceDirect