Navarre, Laure; Martinez, Remi; Genet, Jean-Pierre; Darses, Sylvain published the artcile< Access to enantioenriched α-amino esters via rhodium-catalyzed 1,4-addition/enantioselective protonation>, HPLC of Formula: 112-63-0, the main research area is amino acid ester asym preparation; aryltrifluoroborate amino acrylate conjugate addition protonation rhodium.
Conjugate addition of potassium trifluoro(organo)borates to dehydroalanine derivatives, mediated by a chiral rhodium catalyst and in situ enantioselective protonation, afforded straightforward access to a variety of protected α-amino esters with high yields and enantiomeric excesses up to 95%. Among the tested chiral ligands and proton sources, Binap, in combination with guaiacol (2-methoxyphenol), an inexpensive and nontoxic phenol, afforded the highest asym. inductions. Organostannanes have also shown to participate in this reaction. By a fine-tuning of the ester moiety, and using Difluorophos as chiral ligand, increased levels of enantioselectivity, generally close to 95%, were achieved. Deuterium labeling experiments revealed, and DFT calculation supported, an unusual mechanism involving a hydride transfer from the amido substituent to the α carbon explaining the high levels of enantioselectivity attained in controlling this α chiral center.
Journal of the American Chemical Society published new progress about Amino acid esters Role: SPN (Synthetic Preparation), PREP (Preparation). 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, HPLC of Formula: 112-63-0.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics