142569-76-4Relevant academic research and scientific papers
Sulfoxide ligand metal catalyzed oxidation of olefins
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, (2019/05/09)
The enantioselective synthesis of isochroman motifs has been accomplished via Pd(II)-catalyzed allylic C—H oxidation from terminal olefin precursors. Critical to the success of this goal was the development and utilization of a novel chiral aryl sulfoxide-oxazoline (ArSOX) ligand. The allylic C—H oxidation reaction proceeds with the broadest scope and highest levels asymmetric induction reported to date (avg. 92% ee, 13 examples ≥90% ee). Additionally, C(sp3)-N fragment coupling reaction between abundant terminal olefins and N-triflyl protected aliphatic and aromatic amines via Pd(II)/sulfoxide (SOX) catalyzed intermolecular allylic C—H amination is disclosed. A range of 52 allylic amines are furnished in good yields (avg. 76%) and excellent regio- and stereoselectivity (avg. >20:1 linear:branched, >20:1 E:Z). For the first time, a variety of singly activated aromatic and aliphatic nitrogen nucleophiles, including ones with stereochemical elements, can be used in fragment coupling stiochiometries for intermolecular C—H amination reactions.
Palladium-Catalyzed Alkylation with Alkyl Halides by C(sp3)?H Activation
Wu, Zhuo,Ma, Ding,Zhou, Bo,Ji, Xiaoming,Ma, Xiaotian,Wang, Xiaoling,Zhang, Yanghui
supporting information, p. 12288 - 12291 (2017/09/06)
Utilizing halogens as traceless directing goups represents an attractive strategy for C?H functionalization. A two C?H alkylation system, initiated by the oxidative addition of organohalides to Pd0, has been developed. The first reaction involves an intermolecular alkylation of palladacycles to form C(sp3)?C(sp2) bonds followed by C(sp2)?H activation/cyclization to deliver alkylated benzocyclobutenes as the final products. In the second reaction, two C?C bonds are formed by the reaction of palladacycles with CH2Br2, and provides a facile and efficient method for the synthesis of indanes. The alkylated benzocyclobutene products can be transformed into tricyclic hyrocarbons, and the indane derivatives are essential structural motifs in bioactive and odorant molecules.
Enantioselective Allylic C?H Oxidation of Terminal Olefins to Isochromans by Palladium(II)/Chiral Sulfoxide Catalysis
Ammann, Stephen E.,Liu, Wei,White, M. Christina
, p. 9571 - 9575 (2016/08/10)
The enantioselective synthesis of isochroman motifs has been accomplished by palladium(II)-catalyzed allylic C?H oxidation from terminal olefin precursors. Critical to the success of this goal was the development and utilization of a novel chiral aryl sul
Phenylacetic acid regioisomers possessing a N-difluoromethyl-1,2-dihydropyrid-2-one pharmacophore: Evaluation as dual inhibitors of cyclooxygenases and 5-lipoxygenase with anti-inflammatory activity
Yu, Gang,Chowdhury, Morshed A.,Abdellatif, Khaled R.A.,Dong, Ying,Praveen Rao,Das, Dipankar,Velazquez, Carlos A.,Suresh, Mavanur R.,Knaus, Edward E.
body text, p. 896 - 902 (2010/09/10)
A novel class of phenylacetic acid regioisomers possessing a N-difluoromethyl-1,2-dihydropyrid-2-one pharmacophore attached to its C-2, C-3 or C-4 position was designed for evaluation as anti-inflammatory (AI) agents. A number of compounds exhibited a com
Rabbit Liver Esterase-Mediated Enantioselective Synthesis of 2-Arylpropanoic Acids
Senanayake, Chris H.,Bill, Timothy J.,Larsen, Robert D.,Leazer, John,Reider, Paul J.
, p. 5901 - 5904 (2007/10/02)
A novel enzymatic resolution of ortho-substituted 2-arylpropanoic acids using rabbit liver esterase is described.The R-enantiomer is obtained by enzymatic hydrolysis of the ethyl ester whereas the S-enantiomer is obtained by enzyme mediated enantioselecti
