162377-68-6Relevant articles and documents
Amino acid chiral ligand containing bidentate coordination group, chiral catalyst, and corresponding preparation methods and applications thereof
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Paragraph 0073, (2019/10/02)
The present invention relates to an amino acid chiral ligand containing a bidentate coordination group, a chiral catalyst, and corresponding preparation methods and applications thereof. The chiral ligand is prepared from a cheap and easily available amino acid, and the development of the chiral ligand can improve the diversity of the chiral ligand. The chiral Ir (III) catalyst is simply and efficiently prepared from the chiral ligand only through a one-step reaction. The chiral Ir (III) catalyst is characterized in that a bidentate guiding group is introduced to an amino acid framework to change the original coordination mode of the amino acid and Ir in order to enhance the chiral control ability of the amino acid to the Ir(III) catalyst. The chiral Ir(III) catalyst is designed and synthesized for the first time, and the selectivity reaches up to 99% ee when the catalyst is successfully applied to the high-efficiency asymmetric synthesis of chiral gamma-cyclolactam, so the catalyst has superior stereo control ability.
Dynamic Kinetic Resolution of N-Protected Amino Acid Esters via Phase-Transfer Catalytic Base Hydrolysis
Yamamoto, Eiji,Wakafuji, Kodai,Furutachi, Yuho,Kobayashi, Kaoru,Kamachi, Takashi,Tokunaga, Makoto
, p. 5708 - 5713 (2018/05/30)
Asymmetric base hydrolysis of α-chiral esters with synthetic small-molecule catalysts is described. Quaternary ammonium salts derived from quinine were used as chiral phase-transfer catalysts to promote the base hydrolysis of N-protected amino acid hexafluoroisopropyl esters in a CHCl3/NaOH (aq) via dynamic kinetic resolution, providing the corresponding products in moderate to good yields (up to 99%) with up to 96:4 er. Experimental and computational mechanistic studies using DFT calculation and pseudotransition state (pseudo-TS) conformational search afforded a TS model accounting for the origin of the stereoselectivity. The model suggested π-stacking and H-bonding interactions play essential roles in stabilizing the TS structures.
Method for preparing tert-leucine and analogues thereof in enantiomeric form and intermediates therein
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, (2008/06/13)
Azlactone (3), or the opposite enantiomer thereof, undergoes biotransformation, using suitable enzymatic activity, in the presence of a compound YH to form a N-acyl-amino acid (2), wherein R1, R2 and R3 are each not hydrogen and are independently selected from groups containing up to 20 carbon atoms, optionally with any combination of R1, R2 and R3 being joined together to form at least one ring, X is selected from groups containing up to 20 carbon atoms, and Y is selected from the group consisting of —OH, -Oalkyl and -Nalkyl. Amino acid (1), or the opposite enantiomer thereof, can be prepared in high enantiomeric excess from N-acyl amino acid (2), by converting Y to OH.