1395414-57-9Relevant academic research and scientific papers
Synthesis of 3,4-diarylsubstituted hexahydro-1H-indoles
Zhou, Feilong,Zhao, Erbao,Yan, Ziqin,Chen, Deheng,Zhao, Yujun
, p. 1871 - 1874 (2018)
Efficient syntheses of 3,4-diarylsubstituted hexahydro-1H-indoles in good yields with excellent diastereoselectivities were achieved with a two-step protocol comprising an allylic cation mediated nucleophilic addition and an intramolecular cyclization rea
Palladium-Catalyzed Asymmetric Tandem Denitrogenative Heck/Tsuji-Trost of Benzotriazoles with 1,3-Dienes
Li, Yin-Lin,Wu, Hai-Hong,Zhang, Junliang,Zhang, Pei-Chao
supporting information, p. 13010 - 13015 (2021/09/07)
The asymmetric denitrogenative cycloaddition has emerged as a powerful tool to build chiral aza-heterocyles. However, only one example of asymmetric denitrogenative cycloaddition of benzotriazole with unsaturated hydrocarbons has been explored so far, bec
Lewis acids promoted 3 + 2 cycloaddition of oxaziridines and cyclic allylic alcohols through carbonyl imine intermediates
Zhao, Erbao,Zhou, Feilong,Zhao, Yujun
, p. 4282 - 4293 (2019/04/30)
Syntheses of isoxazolidines through the carbonyl imine intermediates are currently limited to monosubstituted olefin substrates. Herein, we reported syntheses of novel bicyclic isoxazolidine-containing compounds through 1,3-dipolar cycloaddition reactions
Palladium-catalyzed oxidative rearrangement of tertiary allylic alcohols to enones with oxygen in aqueous solvent
Li, Jingjie,Tan, Ceheng,Gong, Jianxian,Yang, Zhen
supporting information, p. 5370 - 5373 (2015/01/09)
A one-pot procedure for Pd(TFA)2-catalyzed 1,3-isomerization of tertiary allylic alcohols to secondary allylic alcohols followed by a Pd(TFA)2/neocuproine-catalyzed oxidative reaction to β-disubstituted-α,β-unsaturated kenones was developed. (Chemical Equation Presented).
Pt-catalyzed oxidative rearrangement of cyclic tertiary allylic alcohols to enones using aqueous hydrogen peroxide
Nagamine, Takashi,Kon, Yoshihiro,Sato, Kazuhiko
supporting information; experimental part, p. 744 - 746 (2012/09/22)
An oxidative rearrangement of cyclic tertiary allylic alcohols to β-disubstituted α,β-unsaturated ketones by Pt black catalyst with aqueous hydrogen peroxide is described. The reaction proceeds under organic solvent- and halide-free conditions and gives only water as a coproduct. The Pt black catalyst is commercially available and can be reused at least four times.
Cu-catalyzed enantioselective 1,4-additions of aryl-Grignard reagents to cyclohexenone in the presence of TADDOL-derived phosphane-phosphite ligands
Naeemi, Qaseem,Dindaroglu, Mehmet,Kranz, Darius P.,Velder, Janna,Schmalz, Hans-Guenther
experimental part, p. 1179 - 1185 (2012/04/10)
Asymmetric conjugate additions (1,4-additions) of aryl-Grignard reagents to cyclohex-2-enone, currently a more or less unsolved challenge, were investigated. For this purpose, a small library of phenol-derived chiral phosphane-phosphite ligands containing TADDOL- or BINOL-based phosphite moieties was evaluated. These ligands are easily prepared by a short modular scheme previously developed in this laboratory. Two particularly powerful ligands (4a and 4b, both TADDOL-derived and each possessing a bulky tert-butyl substituent ortho to the phosphite group) were identified. Conditions were optimized with use of the addition of (4-methoxyphenyl)magnesium bromide to cyclohexenone as a standard reaction system. Under optimized conditions [CuBr·SMe 2 (4 mol-%), ligand 4a (6 mol-%), 2-methyl-THF, -78 °C, slow addition of Grignard reagent] the 1,4-product was obtained with high enantioselectivity (up to 95 % ee) and good regioselectivity (r.r. = 90:10). The scope of the method was probed with different aryl-Grignard reagents. It was found that reagents with electron-donating substituents in meta- or para-positions performed particularly well, whereas the presence of F or CF 3 substituents led to decreased ee values. Only ortho-substituted aryl-Grignard reagents did not give rise to useful results. A series of phosphane-phosphite ligands were also tested in the Rh-catalyzed 1,4-addition of phenylboronic acid to cyclohexenone, but enantioselectivities did not exceed 70 % ee in this case. The difficult task of employing aryl-Grignard reagents in Cu-catalyzed enantioselective 1,4 addition reactions was achieved with the assistance of readily accessible chiral modular P,P ligands. High enantioselectivities were obtained in a number of synthetically relevant cases. Copyright
