3010-05-7Relevant articles and documents
Iron-catalyzed reductive strecker reaction
Yan, Fachao,Huang, Zijun,Du, Chen-Xia,Bai, Jian-Fei,Li, Yuehui
, p. 188 - 194 (2021/02/03)
Strecker reaction is widely applied for the synthesis of amino acids from aldehydes, amines and cyanides. Herein, we report the FeI2-catalyzed reductive Strecker type reaction of formamides instead of aldehydes to produce amino acetonitriles. The challenging capture of carbinolamine intermediates by CN? was achieved via Fe catalysis. This approach afforded better yields than the use of Ir- or Rh-catalysts. The application ability of this methodology is demonstrated by 1) one-pot construction of (13C labeled) complex molecules from CO2 via amino acetonitrile intermediates and 2) convenient production of homologated carboxylic acids from aldehydes.
Dynamics in Catalytic Asymmetric Diastereoconvergent (3 + 2) Cycloadditions with Isomerizable Nitrones and α-Keto Ester Enolates
Adachi, Masaya,Akakabe, Mai,Ezawa, Tetsuya,Hashizume, Daisuke,Koshino, Hiroyuki,Sodeoka, Mikiko,Sohtome, Yoshihiro
supporting information, p. 9094 - 9104 (2021/07/01)
Reaction design in asymmetric catalysis has traditionally been predicated on a structurally robust scaffold in both substrates and catalysts, to reduce the number of possible diastereomeric transition states. Herein, we present the stereochemical dynamics in the Ni(II)-catalyzed diastereoconvergent (3 + 2) cycloadditions of isomerizable nitrile-conjugated nitrones with α-keto ester enolates. Even in the presence of multiple equilibrating species, the catalytic protocol displays a wide substrate scope to access a range of CN-containing building blocks bearing adjacent stereocenters with high enantio- and diastereoselectivities. Our computational investigations suggest that the enantioselectivity is governed in the deprotonation process to form (Z)-Ni-enolates, while the unique syn addition is mainly controlled by weak noncovalent bonding interactions between the nitrone and ligand.
Design and optimization of a series of 4-(3-azabicyclo[3.1.0]hexan-3-yl)pyrimidin-2-amines: Dual inhibitors of TYK2 and JAK1
Ambler, Catherine M.,Arnold, Eric,Banker, Mary Ellen,Clark, James D.,Dowty, Martin E.,Efremov, Ivan V.,Fensome, Andrew,Flick, Andrew,Gerstenberger, Brian S.,Gifford, Roger S.,Gopalsamy, Ariamala,Hegen, Martin,Jussif, Jason,Limburg, David C.,Lin, Tsung H.,Pierce, Betsy S.,Sharma, Raman,Trujillo, John I.,Vajdos, Felix F.,Vincent, Fabien,Wan, Zhao-Kui,Xing, Li,Yang, Xiaojing,Yang, Xin
supporting information, (2020/04/15)
Herein, we disclose a new series of TYK2/ JAK1 inhibitors based upon a 3.1.0 azabicyclic substituted pyrimidine scaffold. We illustrate the use of structure-based drug design for the initial design and subsequent optimization of this series of compounds. One advanced example 19 met program objectives for potency, selectivity and ADME, and demonstrated oral activity in the adjuvant-induced arthritis rat model.
