37137-00-1Relevant articles and documents
CuCl2-Mediated Oxidative Intramolecular α-Arylation of Ketones with Phenolic Nucleophiles via Oxy-Allyl Cation Intermediates
Aota, Yusuke,Kano, Taichi,Maruoka, Keiji,Mochimatsu, Takuto
supporting information, p. 3816 - 3819 (2020/10/19)
α-Functionalization of ketones in an umpolung fashion can be achieved by nucleophilic addition to the oxy-allyl cation intermediate. However, applicable carbon nucleophiles are limited to ones with high nucleophilicity. Additionally, introduction of a lea
Ni-Catalyzed Enantioselective Conjunctive Coupling with C(sp3) Electrophiles: A Radical-Ionic Mechanistic Dichotomy
Lovinger, Gabriel J.,Morken, James P.
supporting information, p. 17293 - 17296 (2017/12/15)
The catalytic enantioselective conjunctive coupling of C(sp3) electrophiles can be accomplished with Ni catalysis. The enantioselectivity of the reaction is dependent on reaction mechanism with many substrates able to engage in an asymmetric process with Pybox-Ni complexes, whereas other substrates provide racemic product mixtures. The link between substrate structure and selectivity is addressed.
Enantioselective synthesis of a highly substituted tetrahydrofluorene derivative as a potent and selective estrogen receptor beta agonist
Maddess, Matthew L.,Scott, Jeremy P.,Alorati, Anthony,Baxter, Carl,Bremeyer, Nadine,Brewer, Sarah,Campos, Kevin,Cleator, Ed,Dieguez-Vazquez, Alejandro,Gibb, Andrew,Gibson, Andrew,Howard, Melissa,Keen, Stephen,Klapars, Artis,Lee, Jaemoon,Li, Jing,Lynch, Joseph,Mullens, Peter,Wallace, Debra,Wilson, Robert
, p. 528 - 538 (2014/05/06)
The development and execution of a practical asymmetric synthesis of the estrogen receptor beta selective agonist (8R,10aS)-6-(trifluoromethyl)-8,9,10, 11-tetrahydro-8,10a-methanocyclohepta[1,2]indeno[4,5-d][1,2,3]triazol-7(3H)-one is described. The optimized route features a key chiral auxiliary-mediated dialkylation approach to set the all-carbon quaternary center with exceptional stereocontrol. Overall, the chemistry has been used to prepare >30 kg of drug candidate in 21% overall yield through 13 longest linear steps and with >99% ee.
Efficient procedures to prepare primary and secondary alkyl halides from alkanols via the corresponding sulfonates under mild conditions
Cahiez, Gerard,Gager, Olivier,Moyeux, Alban,Delacroix, Thomas
supporting information; experimental part, p. 1519 - 1528 (2012/07/03)
The study presented herein shows that sulfonate/halide exchange can be advantageously performed in THF to avoid several side reactions such as elimination and epimerization when the reaction is performed from a chiral alkyl sulfonate or a substrate having a C-H acidic chiral center. The main limitation of this procedure was found to be the conversion of secondary alkyl sulfonates to alkyl chlorides. In this case, the addition of a catalytic amount of manganese chloride clearly accelerates the rate and the efficiency of the reaction. Copyright
Substituted N-phenoxyethylanilines: preparation and acid-base properties evaluation by fluorescence spectrometry
Autino, Juan C.,Bruzzone, Liliana,Romanelli, Gustavo P.,Jios, Jorge L.,Ancinas, Horacio A.
, p. 292 - 294 (2007/10/03)
Representative substituted N-phenoxyethylanilines were prepared starting on 1-bromo- or 1-iodo-2-phenoxyethanes and anilines in DMSO as the solvent, in mild reaction conditions. The acid dissociation constants of the N-aryl N-(2-aryloxyethyl) ammonium ion