65027-12-5Relevant academic research and scientific papers
Biocatalytic Synthesis of Chiral N-Functionalized Amino Acids
Hyslop, Julia F.,Lovelock, Sarah L.,Sutton, Peter W.,Brown, Kristin K.,Watson, Allan J. B.,Roiban, Gheorghe-Doru
supporting information, p. 13821 - 13824 (2018/09/27)
N-Functionalized amino acids are important building blocks for the preparation of diverse bioactive molecules, including peptides. The development of sustainable manufacturing routes to chiral N-alkylated amino acids remains a significant challenge in the pharmaceutical and fine-chemical industries. Herein we report the discovery of a structurally diverse panel of biocatalysts which catalyze the asymmetric synthesis of N-alkyl amino acids through the reductive coupling of ketones and amines. Reactions have been performed on a gram scale to yield optically pure N-alkyl-functionalized products in high yields.
Competing benzyl cation transfers in the gas-phase fragmentation of the protonated benzyl phenylalaninates
Li, Fei,Wu, Yanqing,Zhang, Ningwen,Jiang, Jianxiong,Jiang, Kezhi
, p. 23 - 29 (2014/06/24)
In this study, the competing benzyl cation transfer reactions have been explored by investigating the gas phase chemistry of the protonated benzyl phenylalaninates. Protonation at the carboxylic O atom results in the breakage of the ester CO bond to afford the benzyl cation, which undergoes the competing migration to the amino N atom or the phenyl ring C atom. Both the amino and the phenyl ring hydrogen atoms can be activated to be mobile due to the electrophilic attack of the transferring benzyl cation, and migration of the activated hydrogen atom to the carboxylic hydroxyl leads to (H2O + CO) elimination of the precursor ion. Interestingly, it is much more preferred for the benzyl cation to transfer to the phenyl ring via the amino N, leading to the stepwise benzyl cation transfer, albeit the amino N atom contains more nucleophilic affinity. The mechanistic processes have been confirmed by the MS3 spectra data, along with D-labeling experiments and theoretical calculations.
Method for producing amines by homogeneously catalyzed reductive amination of carbonyl compounds
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Page/Page column 15-16, (2010/02/11)
The invention relates to the preparation of chiral or achiral amines by reaction of aldehydes or ketones with ammonia or primary or secondary amines in the presence of hydrogen and in the presence of homogeneous metal catalysts under mild conditions. Metal catalysts which can be used are complexes of late transition metals with chiral or achiral phosphorus-containing ligands.
On the reductive amination of aldehydes and ketones catalyzed by homogeneous Rh(I) complexes
Tararov,Kadyrov,Riermeier,Borner
, p. 1867 - 1868 (2007/10/03)
The homogeneously catalyzed reductive amination of aldehydes and ketones under smooth conditions is reported, showing for the first time, that Rh(I) catalysts based on chelating diphosphines and diphosphinites can be advantageously employed for this reaction, even for the production of chiral amino acid derivatives.
