research article

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

Couturier, Cedric
•
Blanchet, Jerome
•
Schlama, Thierry
Show more
2006
Organic Letters

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)]

Type
research article
DOI
10.1021/ol060700u
Author(s)
Couturier, Cedric
Blanchet, Jerome
Schlama, Thierry
Zhu, Jieping  
Date Issued

2006

Published in
Organic Letters
Volume

8

Issue

10

Start page

2183

End page

2186

Subjects

Asymmetric synthesis and induction; Nucleophiles (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); Carbanions 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); Amino acids Role: SPN (Synthetic preparation)

•

PREP (Preparation) (esters; 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)

•

amino ester beta enantiopure asym synthesis aziridinium intermediate; serine Me ester dibenzylmethylsulfonyl heteronucleophile carbanion

Note

CAN 145:28222

34-2

Amino Acids, Peptides, and Proteins

Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.

Journal

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)

Editorial or Peer reviewed

REVIEWED

Written at

OTHER

EPFL units
LSPN  
Available on Infoscience
November 25, 2010
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/58451