192123-40-3Relevant academic research and scientific papers
Practical synthesis of enantiomerically pure β2-amino acids via proline-catalyzed diastereoselective aminomethylation of aldehydes
Chi, Yonggui,English, Emily P.,Pomerantz, William C.,Horne, W. Seth,Joyce, Leo A.,Alexander, Lane R.,Fleming, William S.,Hopkins, Elizabeth A.,Gellman, Samuel H.
, p. 6050 - 6055 (2008/02/08)
Proline-catalyzed diastereoselective aminomethylation of aldehydes using a chiral iminium ion, generated from a readily prepared precursor, provides α-substituted-β-amino aldehydes with 85:15 to 90: 10 dr. The α-substituted-β-amino aldehydes can be reduce
CONCISE BETA2-AMINO ACID SYNTHESIS VIA ORGANOCATALYTIC AMINOMETHYLATION
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Page/Page column 51-52, (2010/11/28)
The present invention provides a method for the synthesis of ?2-amino acids. The method also provides methods yielding a-substituted ?-amino aldehydes and ?-substituted γ-amino alcohols. The present method according to this invention allows for increased yield and easier purification using minimal chromatography or crystallization. The methods described herein are based on an aldehyde aminomethylation which involves a Mannich reaction between an aldehyde and a formaldehyde-derived N,O-acetal (iminium precursor) and a catalyst, such as, for example, L-proline or a pyrrolidine. The invention allows for large scale, commercial preparation of ?2-amino acids.
Building units for N-backbone cyclic peptides. Part 4. Synthesis of protected Nα-functionalized alkyl amino acids by reductive alkylation of natural amino acids
Bitan, Gal,Muller, Dan,Kasher, Ron,Gluhov, Evgenia V.,Gilon, Chaim
, p. 1501 - 1510 (2007/10/03)
A new method for the synthesis of protected Nα-(ω-Y-alkyl) amino acids (Y is a thio, amino or carboxy group) and related compounds by reductive alkylation of natural amino acids is reported. These new amino acids serve as building units for the synthesis of backbone-cyclic peptides. They are orthogonally protected at the α-amino position by butoxycarbonyl (Boc) or 9-fluorenylmethoxycarbonyl (Fmoc), using trimethylsilyl temporary protection, to allow for their incorporation into peptides by solid phase peptide synthesis.
