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Control of diastereoselectivity in alkylation of chiral lithium enolates mediated by a chiral secondary amine ligand

โœ Scribed by Yoshihiro Hasegawa; Hisashi Kawasaki; Kenji Koga

Book ID
104225005
Publisher
Elsevier Science
Year
1993
Tongue
French
Weight
275 KB
Volume
34
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Diasterwselective akylation of chital lithium etwlates (dl-, (R)-and (S)-9) derivedjbm 4-t-butykycioh in the presence da chiral secondary amine (R)_I and litkium bromide was studied., It is shown that (R)-1 re t&a&s the direction of tke attack of electrophi~s. stereoselective axial attack ws oL erved on (R)-9, while equatoriul attack on (S)3. Thus highly

The present metkod provides an @cient procedure for the asymmetric synthesis of 2,4-disubstitttted &OhtXWWttt?S.

๐Ÿ“œ SIMILAR VOLUMES

Construction of chiral quaternary carbon
Construction of chiral quaternary carbon centers by asymmetric alkylation of achiral lithium enolates mediated by chiral tetradentate ligands: Stoichiometric and catalytic approaches
โœ Yasuhiro Yamashita; Kazunori Odashima; Kenji Koga ๐Ÿ“‚ Article ๐Ÿ“… 1999 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 217 KB

Enantioselective asymmetric alkylation of achiral lithium enolates mediated by chiral tetradentate amine ligands is achieved to give chiral quaternary carbon centers. Turnover of a chiral tetradentate amine in the presence of an achiral bidentate amine during the reaction is also realized.