182137-24-2

Upstream product

• 501-53-1 benzyl chloroformate 
• 90741-33-6 (2S)-1-benzyl-(E)-5-<(methoxycarbonyl)methylidene>proline tert-butyl ester 
• 90741-31-4 (S)-N-benzyl-5-thioxoproline tert-butyl ester 
• 81477-94-3 N-(diphenylmethylene)glycine tert-butyl ester 
• 939387-21-0 7-tert-butyl (E)-(S)-1-methyl-6-(diphenylmethyleneamino)hept-3-enedioate 

Downstream Products

• 178813-40-6 (2S,5R)-5-(2-Hydroxy-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 
• 113472-56-3 (2S)-cis-1-(benzyloxycarbonyl)-5-vinylproline tert-butyl ester 
• 182137-38-8 (2S,5R)-5-(2-Bromo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 
• 182137-69-5 (2S,5R)-5-(2-Phenylselanyl-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 
• 182137-68-4 (2S,5R)-5-(2-Methanesulfonyloxy-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 
• 182138-57-4 (1S,3S,4R)-3-Triethylsilanyloxy-7-aza-bicyclo[2.2.1]heptane-1,7-dicarboxylic acid 7-benzyl ester 1-tert-butyl ester 
• 182266-45-1 (2S,5R)-(R)-5-Oxiranyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 
• 182137-71-9 (2S,5R)-(S)-5-Oxiranyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 
• 182137-73-1 (2S,5R)-5-((S)-2-Bromo-1-triethylsilanyloxy-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 
• 182266-46-2 (2S,5R)-5-((R)-2-Bromo-1-triethylsilanyloxy-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 

Relevant academic research and scientific papers

Organocatalytic asymmetric 1,6-additions of β-ketoesters and glycine imine

The first organocatalytic enantioselective 1,6-addition of β-ketoesters and benzophenone imine to electron-poor δ-unsubstituted dienes using cinchona alkaloids under phase-transfer conditions is demonstrated. The scope of the reaction for the β-ketoesters

Chirospecific synthesis of conformationally constrained 7-azabicycloheptane amino acids by transannular alkylation

A new method is reported for the chirospecific preparation of optically pure 1-carboxy-7-azabicycloheptane amino acids for the generation of peptidomimetics as conformational probes. The method allows for the multigram preparation of these amino acid analogues through use of a thiolactam sulfide contraction and a transannular alkylation sequence as the key C-C bond-forming steps, starting from L-glutamic acid. The route provides access to two common intermediates, 7-(benzyloxycarbonyl)-1-carboxy-7-azabicyclo[2.2.1]-3-heptane and (1S,4R)-7-(benzyloxycarbonyl)-1-carboxy-7-azabicyclo[2.2.1]-3-heptanon e tert-butyl ester, for elaboration to symmetrical and chiral amino acid homologues, respectively. Decarboxylation of the C-1 carboxy unit of the latter intermediate also demonstrated the applicability of the method for a short, chirospecific preparation of a (+)-epibatidine intermediate, (1S,4R)-7-(tert-butyloxycarbonyl)-1-carboxy-7-azabicyclo[2.2.1]3-hepta none.