143919-84-0Relevant articles and documents
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 (1994)
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.
Stereoselective addition of alkyl- or phenylaluminium dichloride to α-alkyl-β-formyl amides providing threo α-alkyl-β-hydroxy amides
Fujii,Taniguchi,Oshima,Utimoto
, p. 4579 - 4580 (2007/10/02)
Treatment of α-alkyl-β-formyl amides with RAlCl2 or PhAlCl2 provided threo-α-alkyl-β-hydroxy amides under high stereocontrol.
SUR LES ORGANOMETALLIQUES ISSUS DE THIOAMIDES. I. REACTIVITE AVEC LES ALDEHYDES ET CETONES; STEREOCHIMIE DE LA CONDENSATION AVEC LA t-BUTYL-4 CYCLOHEXANONE ET LE BENZALDEHYDE
Goasdoue, Claude,Goasdoue, Nicole,Gaudemar, Marcel,Mladenova, Margarita
, p. 279 - 292 (2007/10/02)
Organometallic compounds derived from thioamides RCH2CSN(R3)2 condense normally with aldehydes and saturated ketones.Condensation with 4-t-butylcyclohexanone leads predominantly to equatorial attack by the organometallic compound.These results suggest that the organometallic structure is RCH=C(SM)N(R3)2.The stereoselectivity of the reaction with benzaldehyde depends on R and R3; a mechanism for the formation of β-hydroxythioamides is discussed.
