861909-30-0Relevant articles and documents
Enantioselective Oxidative Homocoupling and Cross-Coupling of 2-Naphthols Catalyzed by Chiral Iron Phosphate Complexes
Narute, Sachin,Parnes, Regev,Toste, F. Dean,Pappo, Doron
, p. 16553 - 16560 (2016/12/27)
Novel chiral iron phosphate complexes were prepared as catalysts for asymmetric oxidative coupling reactions. These catalysts were applied for the synthesis of enantio-enriched C1- and C2-symmetric BINOLs, in which the 3 and 3′ positions are available for chemical modifications. It was proposed that the reaction takes place via an oxidative radical-anion coupling mechanism. A destructive BINOL racemization that competes with the enantioselective oxidative coupling of 2-naphthols was revealed, thereby offering new insights into this highly important reaction.
Synthesis of novel chiral phosphoric acid-bearing two acidic phenolic hydroxyl groups and its catalytic evaluation for enantioselective Friedel-Crafts alkylation of indoles and enones
Liu, Xiong-Li,Yu, Zhang-Biao,Pan, Bo-Wen,Chen, Lin,Feng, Ting-Ting,Zhou, Ying
, p. 628 - 634 (2015/03/30)
A novel chiral phosphoric acid catalyst bearing two acidic phenolic hydroxyl groups was synthesized. Its catalytic activity as a chiral Br?sted acid has been examined in the enantioselective Friedel-Crafts alkylation of indoles and enones as a model reaction. In comparison with the other chiral phosphoric acid catalysts, the reaction catalyzed by the novel chiral catalyst afforded the desired 3-substituted indoles in a higher enantioselectivity (up to 69% ee).
Enantioselective organocatalytic fluorination-induced Wagner-Meerwein rearrangement
Romanov-Michailidis, Fedor,Guénée, Laure,Alexakis, Alexandre
, p. 9266 - 9270 (2013/09/12)
Cracked under strain: Strained allylic cyclobutanols and cyclopropanols readily undergo a ring expansion described by the title rearrangement. This reaction is promoted by catalytic amounts of 1 and displays high tolerance with respect to the substrate scope. The corresponding β-fluoro spiroketone products are isolated in high yields and with excellent stereoselectivities. EDG=electron-donating group, EWG=electron-withdrawing group. Copyright
A protecting-group-free route to chiral BINOL-phosphoric acids
Li, Baojian,Chiu, Pauline
, p. 3932 - 3937 (2011/09/14)
A two-step, protecting group-free route for the synthesis of 3,3′-disubstituted and 6,6′-disubstituted chiral BINOL-phosphoric acids has been realized starting from commercially available brominated BINOLs. This synthesis relies on the direct Suzuki coupl
Enantioselective direct aza hetero-Diels-Alder reaction catalyzed by chiral Bronsted acids
Liu, Hua,Cun, Lin-Feng,Mi, Ai-Qiao,Jiang, Yao-Zhong,Gong, Liu-Zhu
, p. 6023 - 6026 (2007/10/03)
(Chemical Equation Presented) The first chiral Bronsted acid-catalyzed asymmetric direct aza hetero-Diels-Alder reaction has been described. The phosphoric acids, prepared from binol and H8-binol derivatives, have shown catalytic ability for th