Tetrahedron

Stereoselective reductive amination of β-keto esters derived from dipeptides. Stereochemical and mechanistic studies on the formation of 5-carboxymethyl-2- …

…, R Herranz, MT García-López, R González-Muñiz

Index: Patino-Molina, Rosario; Herranz, Rosario; Garcia-Lopez, M. Teresa; Gonzalez-Muniz, Rosario Tetrahedron, 1999 , vol. 55, # 52 p. 15001 - 15010

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Citation Number: 14

Abstract

The stereoselective generation of 3, 5-disubstituted and 3, 5, 6-trisubstituted 2- oxopiperazine derivatives can be accomplished by intramolecular reductive amination of β- keto esters derived from Z-Xaa-Gly-OH and Z-Xaa-Yaa-OH dipeptides, respectively. Differences in the stereoselectivity between the use of NaBH3CN and hydrogen as reducing agents are due to the reduction of different intermediates, as deduced from experiments of ...