6312-02-3Relevant academic research and scientific papers
PIPERIDIN-1- YL-N-PYRYDI NE-3-YL-2-OXOACET AM IDE DERIVATIVES USEFUL FOR THE TREATMENT OF MTAP-DEFICIENT AND/OR MT A-ACCUMULATING CANCERS
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, (2022/02/09)
Compounds are provided according to Formula (I) and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein R1, R2, R3, R4, R6, R7, R8 and n are as defined herein. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of conditions.
General Light-Mediated, Highly Diastereoselective Piperidine Epimerization: From Most Accessible to Most Stable Stereoisomer
Shen, Zican,Walker, Morgan M.,Chen, Shuming,Parada, Giovanny A.,Chu, Duc M.,Dongbang, Sun,Mayer, James M.,Houk,Ellman, Jonathan A.
supporting information, p. 126 - 131 (2021/01/12)
We report a combined photocatalytic and hydrogen atom transfer (HAT) approach for the light-mediated epimerization of readily accessible piperidines to provide the more stable diastereomer with high selectivity. The generality of the transformation was explored for a large variety of di- to tetrasubstituted piperidines with aryl, alkyl, and carboxylic acid derivatives at multiple different sites. Piperidines without substitution on nitrogen as well as N-alkyl and aryl derivatives were effective epimerization substrates. The observed diastereoselectivities correlate with the calculated relative stabilities of the isomers. Demonstration of reaction reversibility, luminescence quenching, deuterium labeling studies, and quantum yield measurements provide information about the mechanism.
Borane-Catalyzed Reduction of Pyridines via a Hydroboration/Hydrogenation Cascade
Yang, Zhao-Ying,Luo, Heng,Zhang, Ming,Wang, Xiao-Chen
, p. 10824 - 10829 (2021/09/08)
We have developed a method for a B(C6F5)3-catalyzed hydroboration/hydrogenation cascade reduction of pyridines. The method was particularly effective for 2,3-disubstituted pyridines, which generated piperidines in high yields with high cis selectivity. Mechanistic studies indicated that the pyridine substrates and the piperidine products sequentially acted as bases in cooperation with B(C6F5)3to split H2. The broad functional group tolerance of the method allowed its use for the synthesis of some biologically active molecules.
Enzyme Cascades in Whole Cells for the Synthesis of Chiral Cyclic Amines
Hepworth, Lorna J.,France, Scott P.,Hussain, Shahed,Both, Peter,Turner, Nicholas J.,Flitsch, Sabine L.
, p. 2920 - 2925 (2017/05/31)
The increasing diversity of reactions mediated by biocatalysts has led to development of multistep in vitro enzyme cascades, taking advantage of generally compatible reaction conditions. The construction of pathways within single whole cell systems is much less explored, yet has many advantages. Herein we report the generation of a successful whole cell de novo enzyme cascade for the diastereoselective and/or enantioselective conversion of simple, linear keto acids into valuable cyclic amine products. The pathway starts with carboxylic acid reduction that triggers a transamination, imine formation, and subsequent imine reduction. Construction and optimization of the system was achieved by standard genetic manipulation and the cascade required only starting material, amine donor, and whole cell catalyst with cofactors provided internally by glucose metabolism. A panel of synthetic keto acids provided access to piperidines in high conversions (up to 93%) and enantiomeric excess (up to 93%).
