380149-34-8

Upstream product

• 479423-40-0 N-tert-butyl 4-methoxybenzylidenecarbamate 
• 4248-19-5 tert-butyl carbazate 
• 123-11-5 4-methoxy-benzaldehyde 
• 741259-87-0 tert-butyl (4-methoxyphenyl)(phenylsulfonyl)methylcarbamate 
• 186581-53-3 diazomethane 
• 124-38-9 carbon dioxide 
• 1415303-94-4 tert-butyl {(dimethylphenylsilyl)(4-methoxyphenyl)methyl}carbamate 
• 1291065-81-0 C₂₅H₄₅NO₃Sn 
• 55362-76-0 2-(tert-butoxycarbonylamino)-2-(4-methoxyphenyl)acetic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 

Relevant academic research and scientific papers

One-pot synthesis of α-amino acids from CO2 using a bismetal reagent with Si-B bond

In the presence of 1.1 equiv of PhMe2Si-Bpin, 5 equiv of CsF, and 20 mol % of TsOH·H2O, precursors of N-Boc-imines can be converted into the corresponding α-aryl or α-alkenyl glycine derivatives under gaseous CO2 in moderate-to-high yields with a single operation. α-Isobutenyl glycine thus obtained can be further derivatized into various types of α-amino acids including N-Boc-leucine, serine, and glycine derivatives in short steps.

Synthesis of arylglycine and mandelic acid derivatives through carboxylations of α-amido and α-acetoxy stannanes with carbon dioxide

Incorporation reactions of carbon dioxide (CO2) with N-Boc-α-amido and α-acetoxy stannanes were developed using CsF as a mild tin activator. Monoprotected α-amido stannanes could be used, and the corresponding arylglycine derivatives were obtained in moderate-to-high yields under 1 MPa (10 atm) of CO2 pressure. α-Acetoxy stannanes also underwent carboxylation to afford mandelic acid derivatives in excellent yields under ambient CO2 pressure. Both transformations enabled the synthesis of α-tertiary and α-quaternary carboxylic acid derivatives. In addition, the chirality of (S)-N-tert-butylsulfonyl-α- amido stannanes was transferred with up to 90% inversion of configuration at 100 °C.