106872-30-4Relevant academic research and scientific papers
Base assisted substitution of α-amidoalkyl sulfones by nitromethane anion. A new entry to functionalized α-amino acids
Ballini, Roberto,Petrini, Marino
, p. 4449 - 4452 (2007/10/03)
The nitromethane anion reacts with α-amidoalkyl sulfones in THF affording the corresponding nitro derivatives that upon oxidation with alkaline potassium permanganate give the corresponding N-protected α-amino acids.
SYNTHESIS OF α-AMINO ACIDS WITH β,γ-UNSATURATED SIDE CHAINS
Castelhano, Arlindo L.,Horne, Stephen,Taylor, Gregg J.,Billedeau, Roland,Krantz, Allen
, p. 5451 - 5466 (2007/10/02)
α-Amino acids with allenyl, vinyl and acetylenic side chains can be synthesized using non-enolate based strategies.The ester enolate-Claisen rearrangement applied to propargylic esters of N-protected α-amino acids is of limited utility since only poor yields of allenic product are obtained with the N-Boc glycine esters, the system which give the most reproducible results.However, α-allenyl-α-amino acids that are fully functionalized on the α-carbon are available through the agency of 4-allenyl-2-phenyloxazolones 4 ( obtained from propargyl esters of N-benzoyl protected amino acids via cyclization and Claisen rearrangement ) provided that Meerwein's reagent is used to facilitate hydrolysis of the benzamide function in 5.A variety of α-substituted glycinates, including those with α-vinyl and α-acetylenic functions, can be prepared using a two step sequence involving condensation of the cationic glycine synthon 22 with various organomagnesium reagents, followed by hydrolysis.
REACTIONS OF AN ELECTROPHILIC GLYCINE CATION EQUIVALENT WITH GRIGNARD REAGENTS A SIMPLE SYNTHESIS OF β,γ-UNSATURATED AMINO ACIDS
Castelhano, Arlindo L.,Horne, Stephen,Billedeau, Roland,Krantz, Allen
, p. 2435 - 2438 (2007/10/02)
A simple and general synthesis of α-amino acids employing vinyl and alkyl Grignard reagents with a glycine cation equivalent is described.
