914400-07-0Relevant articles and documents
A new entry to Pd-H chemistry: Catalytic asymmetric conjugate reduction of enones with EtOH and a highly enantioselective synthesis of warfarin
Tsuchiya, Yasunori,Hamashima, Yoshitaka,Sodeoka, Mikiko
, p. 4851 - 4854 (2006)
(Chemical Equation Presented) We report here the catalytic asymmetric conjugate reduction of enones using ethanol as a hydride source. The reaction was carried out in the presence of a chiral Pd complex at ambient temperature in ethanol, and the desired products were obtained in high chemical yield and high enantioselectivity. We applied this novel reaction to the catalytic asymmetric synthesis of warfarin (96% ee), and on the basis of d-labeling experiments, the reaction mechanism is proposed.
The synthesis of non-racemic β-alkyl-β-aryl-disubstituted allyl alcohols and their transformation into allylamines and amino acids bearing a quaternary stereocenter
Narczyk, Aleksandra,Pieczykolan, Micha?,Stecko, Sebastian
, p. 3921 - 3946 (2018/06/08)
A synthesis of non-racemic β-alkyl-β-aryl allyl alcohols and their transformation into allylamines bearing a quaternary stereogenic center is reported. The allyl alcohols were prepared either by Cu-catalyzed enantioselective reduction of enones or by sequ
Highly enantioselective asymmetric hydrogenation of (E)-β,β- disubstituted α,β-unsaturated Weinreb amides catalyzed by Ir(i) complexes of SpinPhox ligands
Shang, Jian,Han, Zhaobin,Li, Yang,Wang, Zheng,Ding, Kuiling
, p. 5172 - 5174 (2012/06/18)
The Ir(i) complexes of chiral spiro phosphino-oxazoline ligands (SpinPhox) have demonstrated good to excellent enantioselectivity in the asymmetric hydrogenation (AH) of a variety of (E)-β,β-disubstituted α,β-unsaturated N-methoxy-N-methylamides, affording the corresponding optically active Weinreb amides with up to 97% ee.
Pd-catalyzed asymmetric hydrogenation of C=C bond of α,β- unsaturated ketones
Wang, Duo-Sheng,Wang, Da-Wei,Zhou, Yong-Gui
supporting information; experimental part, p. 947 - 950 (2011/06/17)
Homogenous palladium-catalyzed asymmetric hydrogenation of C=C double bond of ,-unsaturated ketones has been -developed by using palladium(II) trifluoroacetate/(S)-7,7-bis-[di(4-methoxyphenyl]phosphino)-1,1-spirobiindane complex [Pd(OCOCF3)2-(S)-An-SDP] as the catalyst under ambient hydrogen pressure and room temperature with up to 89% ee. Georg Thieme Verlag Stuttgart · New York.
Highly chemo- And enantioselective hydrogenation of linear α,β-unsaturated ketones
Lu, Sheng-Mei,Bolm, Carsten
supporting information; experimental part, p. 7513 - 7516 (2009/09/06)
A study was conducted to report the synthesis of sulfoximine-derived P,N-ligands and their applications in indium-catalyzed asymmetric hydrogenation reactions. Investigations were conducted using linear β,β- disubstituted 1,3-diphenyl-2-butenone as model substrate and iridium, having a ketonic phenyl group and two alkyl substituents at the olefinic β-positions. Methyl ketone with β-methyl and β-phenyl substituent was also applied in the investigations.
Asymmetric conjugate reduction of α,β-unsaturated ketones and esters with chiral rhodium(2,6-bisoxazolinylphenyl) catalysts
Kanazawa, Yoshinori,Tsuchiya, Yasunori,Kobayashi, Kazuki,Shiomi, Takushi,Itoh, Jun-Ichi,Kikuchi, Makoto,Yamamoto, Yoshihiko,Nishiyama, Hisao
, p. 63 - 71 (2007/10/03)
New asymmetric conjugate reduction of β,β-disubstituted α,β-unsaturated ketones and esters was accomplished with alkoxylhydrosilanes in the presence of chiral rhodium(2,6-bisoxazolinylphenyl) complexes in high yields and high enantioselectivity. (E)-4-Phenyl-3-penten-2- one and (E)-4-phenyl-4-isopropyl-3-penten-2-one were readily reduced at 60°C in 95% ee and 98 % ee, respectively, by 1 mol % of catalyst loading. (EtO) 2MeSiH proved to be the best hydrogen donor of choice. tert-Butyl (E)-β-methylcinnamate and β-isopropylcinnamate could also be reduced to the corresponding dihydrocinnamate derivatives up to 98% ee.
