Aziridinium from N,N-dibenzyl serine methyl ester: Synthesis of enantiomerically pure beta -amino and alpha ,beta -diamino esters

Reaction of N,N-dibenzyl-O-methylsulfonyl serine Me ester with a variety of heteronucleophiles (sodium azide, sodium phthalimide, amines, thiols) and carbanions (sodium malonate) gave, via an aziridinium intermediate, the corresponding beta -amino or alpha ,beta -diamino ester in good to excellent yield. A short synthesis of orthogonally protected and enantiomerically pure 2,3-diamino propionate (Dap) is described. [on SciFinder (R)]


Published in:
Organic Letters, 8, 10, 2183-2186
Year:
2006
Keywords:
Note:
CAN 145:28222
34-2
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
1523-7060
written in English.
75-64-9; 103-49-1; 108-59-8 (Dimethylmalonate); 110-89-4 (Piperidine); 110-91-8 (Morpholine); 123-90-0 (Thiomorpholine); 288-32-4 (1H-Imidazole); 507-09-5 (Ethanethioic acid); 1074-82-4; 2365-48-2; 2577-48-2; 2759-28-6; 26628-22-8 (Sodium azide); 35161-71-8 Role: RCT (Reactant), RACT (Reactant or reagent) (asym. synthesis of enantiopure beta -amino and alpha ,beta -diamino esters via aziridinium intermediate prepd. by reaction of dibenzylmethylsulfonyl serine Me ester with heteronucleophiles and carbanions); 202478-34-0P; 888957-31-1P; 888957-32-2P; 888957-33-3P; 888957-42-4P; 888957-43-5P; 888957-44-6P; 888957-55-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (asym. synthesis of enantiopure beta -amino and alpha ,beta -diamino esters via aziridinium intermediate prepd. by reaction of dibenzylmethylsulfonyl serine Me ester with heteronucleophiles and carbanions); 61040-20-8P; 888957-34-4P; 888957-35-5P; 888957-36-6P; 888957-37-7P; 888957-38-8P; 888957-39-9P; 888957-40-2P; 888957-41-3P; 888957-45-7P; 888957-46-8P; 888957-47-9P; 888957-48-0P; 888957-49-1P; 888957-50-4P; 888957-51-5P; 888957-52-6P; 888957-53-7P; 888957-54-8P Role: SPN (Synthetic preparation), PREP (Preparation) (asym. synthesis of enantiopure beta -amino and alpha ,beta -diamino esters via aziridinium intermediate prepd. by reaction of dibenzylmethylsulfonyl serine Me ester with heteronucleophiles and carbanions)
Laboratories:




 Record created 2010-11-25, last modified 2018-03-17


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