Stereoselective Addition of Organoaluminium or Organomanganese Reagents to α-Formyl Amides or α-Methyl-Substituted β-Keto Amides
- 1 September 1994
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 67 (9) , 2514-2521
- https://doi.org/10.1246/bcsj.67.2514
Abstract
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.Keywords
This publication has 22 references indexed in Scilit:
- Stereoselective reduction of 2-methyl-3-oxo esters (or amides) with sodium borohydride catalyzed by manganese(II) chloride or tetrabutylammonium borohydride. A practical preparation of erythro and threo-3-hydroxy-2-methyl esters (or amides)Tetrahedron, 1993
- Stereoselective addition of alkyl- or phenylaluminium dichloride to α-alkyl-β-formyl amides providing threo α-alkyl-β-hydroxy amidesTetrahedron Letters, 1992
- Stereoselective addition of organoaluminium or organomanganese reagents to 2-methyl-3—oxo amides (or esters) providing erythro or threo 2-methyl-3-hydroxy amides (or esters)Tetrahedron Letters, 1992
- A practical and stereoselective reduction of 3-keto-2-methyl esters or 3-keto-2-methyl amides into erythro-3-hydroxy-2-methyl esters or erythro-3-hydroxy-2-methyl amides with NaBH4 catalyzed by MnCl2Tetrahedron Letters, 1991
- Highly stereoselective reduction of .alpha.-substituted .beta.-keto amides by means of hydrosilane-fluoride ion and hydrosilane-acid reagent. A practical approach to aldols of both threo and erythro configurationsJournal of the American Chemical Society, 1985
- Highly -diastereoselective reduction of 2-alkyl-3-oxo amides by potassium triethylborohydrideTetrahedron Letters, 1985
- Cerium chloride-promoted nucleophilic addition of grignard reagents to ketones an efficient method for the synthesis of tertiary alcoholsTetrahedron Letters, 1985
- Organocerium reagents. Nucleophilic addition to easily enolizable ketonesTetrahedron Letters, 1984
- Stereoselective reduction of 3-oxo amides with zinc borohydrideTetrahedron Letters, 1983
- Stereoselective reduction of β-keto esters with zinc borohydride. stereoselective synthesis of -3-hydroxy-2-alkylpropionatesTetrahedron Letters, 1980