20428-71-1Relevant articles and documents
Highly diastereoselective synthesis of β-hydroxy amides from β-keto amides
Bartoli, Giuseppe,Bosco, Marcella,Marcantoni, Enrico,Massaccesi, Massimo,Rinaldi, Samuele,Sambri, Letizia
, p. 3092 - 3096 (2007/10/03)
β-Hydroxy amides with stereodefined geometry represent an important unit present in various natural products. The diastereoselective preparation of amides carrying a secondary or tertiary alcohol in β-position is described here.
One-pot highly stereoselective reduction of β-keto amides to syn-γ-aminols
Bartoli, Giuseppe,Bosco, Marcella,Dalpozzo, Renato,Marcantoni, Enrico,Massaccesi, Massimo,Rinaldi, Samuele,Sambri, Letizia
, p. 8811 - 8815 (2007/10/03)
In the presence of titanium tetrachloride, the borane/tetrahydrofuran complex can reduce 2-methyl-3-oxoamides into the corresponding syn-aminols in good yields and high diastereoselectivity. The use of borane/dimethyl sulfide instead of BH3/THF
Stereoselective Addition of Organoaluminium or Organomanganese Reagents to α-Formyl Amides or α-Methyl-Substituted β-Keto Amides
Taniguchi, Masahiko,Fujii, Hideaki,Oshima, Koichiro,Utimoto, Kiitiro
, p. 2514 - 2521 (2007/10/02)
Treatment of α-formyl amides with RAlCl2 or PhAlCl2 provided threo-α-alkyl-substituted β-hydroxy amides under high stereocontrol.The method was successfully applied to the selective addition of alkyl group to α-methyl-substituted β-keto amides or esters.Treatment of α-methyl-β-keto amides or α-methyl-β-keto esters with trialkylaluminium or alkylmanganese halide afforded the corresponding erythro (or threo) α-methyl-substituted β-hydroxy amides or α-methyl-substituted β-hydroxy esters with high stereoselectivity.