219870-38-9

Upstream product

• 219870-21-0 tert-butyl (4R)-4-((1E)-3-methyl-3-phenyl-3-silabut-1-enyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 162107-48-4 tert-butyl (R)-4-ethynyl-2,2-dimethyloxazolidine-3-carboxylate 
• 219870-32-3 tert-butyl (4R)-2,2-dimethyl-4-(3-methyl-3-phenyl-3-silabutyl)-1,3-oxazolidine-3-carboxylate 

Downstream Products

• 258351-86-9 methyl (2R)-2-[(tert-butoxy)carbonylamino]-4-hydroxybutanoate 
• 219870-51-6 methyl (2R)-2-[(tert-butoxy)carbonylamino]-5-methyl-5-phenyl-5-silahexanoate 
• 67198-86-1 (R)-2-[(tert-butoxycarbonyl)amino]butano-4-lactone 
• 219870-45-8 2-tert-butoxycarbonylamino-4-(dimethyl-phenyl-silanyl)-butyric acid 

Relevant academic research and scientific papers

Silylcupration of (R)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4- ethynyloxazolidine: A stereoselective approach to the synthesis of γ- silylated saturated and unsaturated α-amino acids

Enantioselective synthesis of γ-silylated amino acids is reported, using a four-step procedure based on the silylcupration of ethynyloxazolidine 2. Silylcuprates 6a-c are highlighted as useful reagents to be employed with enantiomerically enriched substrates. Vinylsilanes 5 are easily prepared and highlighted as useful intermediates to yield the final compounds after reduction, opening of the oxazolidine ring, and oxidation. Moreover, β,γ- unsaturated amino acids are obtained as very interesting vinylglycine derivatives. The capability of silicon-containing amino acids to be incorporated into dipeptides is also shown.

A stereoselective approach to the synthesis of γ-silylated amino acids

The synthesis of enantiomerically enriched silicon containing amino acids is described. Silylcupration of 2,2-dimethyl-3-(tert-butoxycarbonyl)- 4-ethynyloxazolidine, easily derived from serine aldehyde, afforded regio- and stereoselectively γ-silylated et