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Asymmetric allylation of aromatic aldehydes catalyzed by chiral phosphoramides prepared from (S)-proline

โœ Scribed by Katsuhiko Iseki; Yoshichika Kuroki; Mie Takahashi; Satoshi Kishimoto; Yoshiro Kobayashi

Book ID
104207648
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
870 KB
Volume
53
Category
Article
ISSN
0040-4020

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โœฆ Synopsis

Chiral phosphoramides prepared from (S)-proline were used to catalyze the allylation and crotylation of aromatic aldehydes with allylic trichlorosilanes in good enantioseleetive yields. Phosphoramides 4d and 4m gave chiral homoallylic alcohols and their enantiomers, respectively, with similar levels of enantioselectivity.

๐Ÿ“œ SIMILAR VOLUMES

Palladium-catalyzed asymmetric allylatio
Palladium-catalyzed asymmetric allylations of aldehydes via (S)-proline allyl ester enamines
โœ Kunio Hiroi; Jun Abe; Kyoko Suya; Shuko Sato ๐Ÿ“‚ Article ๐Ÿ“… 1989 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 238 KB

Treatment of chiral enamine 3, derived from (S)-proline ally1 ester (I\_) and 2-phenylpropionaldehyde (z), with tetrakis(triphenylphosphine)palladium provided (R)-(-)-2-methyl-2-phenyl-4-pentenylaldehyde (2) with high enantiomeric excess. The mechanism for this asymmetric induction is discussed.