84653-74-7Relevant academic research and scientific papers
Unusual Effect of a Mixed Solvent on the Asymmetric Reduction of Chiral α-Keto-amides with Sodium Borohydride
Soai, Kenso,Komiya, Kazuyuki,Shigematsu, Yasuhiko,Hasegawa, Hitoshi,Ookawa, Atsuhiro
, p. 1282 - 1283 (1982)
The mixed solvent tetrahydrofuran + methanol (99 : 1) was much more effective than the individual solvents in the asymmetric reduction of chiral α-keto-amides with sodium borohydride; this solvent effect in asymmetric induction is unprecedented.
Stereochimie de la reduction electrochimique d'α-cetoamides optiquement actives II. Electroreduction de benzoylformamides derives de la S(-)-proline
Boulmedais, Ali,Jubault, Michel,Tallec, Andre
, p. 185 - 191 (2007/10/02)
Electrochemical reduction of benzoylformamides derived from S-(-)-proline has been carried out at a mercury cathode in a buffered hydroalcoholic medium; quantitative formation of a mixture of the two epimers of the corresponding mandelamides is observed.D
Asymmetric Synthesis of the Both Enantiomers of α-Hydroxy Acids by the Diastereoselective Reduction of Chiral α-keto Amides with (Complex) Metal Hydrides in the Presence of Metallic Salt
Soai, Kenso,Isoda, Takeshi,Hasegawa, Hitoshi,Ishizaki, Miyuki
, p. 1897 - 1900 (2007/10/02)
Effects of the metallic salts and the reducing reagents in the diastereoselective reduction of chiral α-keto amides derived from (S)-proline methyl ester were examined.Lithium borohydride afforded (S)-α-hydroxy acids, whereas diisobutylaluminum hydride afforded (R)-isomers.In the presence of lithium bromide, reduction with LiBH4 afforded (S)-mandelic acid in over 80 percent e.e.
Diastereoselective Reduction of Chiral α-Ketoamides Derived from (S)-Proline Esters with Sodium Borohydride. Preparation of Optically Active α-Hydroxy Acids
Soai, Kenso,Hasegawa, Hitoshi
, p. 769 - 772 (2007/10/02)
Diastereoselective reductions of chiral α-ketoamides (3) derived from (S)-proline esters (2) with sodium borohydride were examined.Hydrolysis of the reduction products afforded optically active α-hydroxy acids (5) in good enantiomeric excesses (e.e.).The most influential factor of the asymmetric induction was the effect of using a mixed hydroxylic and non-hydroxylic solvent.The degree of asymmetric induction varied considerably with the ratio of alcohol and tetrahydrofuran (THF) in the mixed solvent.With aromatic ketoamides (3), higher asymmetric induction occured in a mixed alcohol-THF solvent than in the corresponding individual solvents.
