Asymmetric Syntheses of (2S,3S,6S)-, (2S,3S,6R)-, and (2R,3R,6S)-2,3-Methano-2,6-diaminopimelic Acids. Studies Directed to the Design of Novel Substrate-based Inhibitors of L,L-Diaminopimelate Epimerase
作者:Robert M. Williams、Glenn J. Fegley、Reneé Gallegos、Felicity Schaefer、David L. Pruess
DOI:10.1016/0040-4020(95)00976-0
日期:1996.1
The asymmetricsyntheses ot (2S,3S,6S)-, (2S,3S,6R)-, and (2R,3R,6S)-2,3-methano-2,6-diaminopimelicacids (7a-c) is described. The synthesis features phosphonate coupling of 13 and 14 to form the corresponding E-olefins which are subsequently cyclopropanated and deprotected under dissolving metal conditions.
New α,β-didehydroamino acid derivatives as precursors in the synthesis of 1-aminocyclopropanecarboxylic acids
作者:Carlos Cativiela、María D. Díaz-de-Villegas、Ana I. Jiménez
DOI:10.1016/s0040-4020(01)85381-3
日期:1994.1
idehydroalanine methyl ester with diazoalkanes or ylides gives the corresponding cyclopropane derivatives in high yields. The cis/trans ratio of these compounds was dependent on substrate, reagent and reaction temperature. From stereochemically homogeneous compounds the corresponding 1-aminocyclopropanecarboxylicacids were easily obtained by acid hydrolysis.