55125-15-0Relevant academic research and scientific papers
Catalytic Asymmetric Synthesis of Unprotected β2-Amino Acids
Zhu, Chendan,Mandrelli, Francesca,Zhou, Hui,Maji, Rajat,List, Benjamin
, p. 3312 - 3317 (2021/04/07)
We report here a scalable, catalytic one-pot approach to enantiopure and unmodified β2-amino acids. A newly developed confined imidodiphosphorimidate (IDPi) catalyzes a broadly applicable reaction of diverse bis-silyl ketene acetals with a silylated aminomethyl ether, followed by hydrolytic workup, to give free β2-amino acids in high yields, purity, and enantioselectivity. Importantly, both aromatic and aliphatic β2-amino acids can be obtained using this method. Mechanistic studies are consistent with the aminomethylation to proceed via silylium-based asymmetric counteranion-directed catalysis (Si-ACDC) and a transition state to explain the enantioselectivity is suggested on the basis of density functional theory calculation.
Primary Aminomethylation at the α-Position of Carboxylic Acids and Esters. Trimethylsilyl Triflate-Catalyzed Reaction of Ketene Silyl Acetals with N,N-Bis(trimethylsilyl)methoxymethylamine
Okano, Kohji,Morimoto, Toshiaki,Sekiya, Minoru
, p. 2228 - 2234 (2007/10/02)
A new, general method for the synthesis of β-aminocarboxylic esters (9) and acids (10) was developed.The introduction of primary aminomethyl unit at the α-position of carboxylic esters (2) and acids (3) was achieved in high yields by the silyl trifluorome
