- Iron-Catalyzed Highly Enantioselective Hydrogenation of Alkenes
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Here, we reported for the first time an iron-catalyzed highly enantioselective hydrogenation of minimally functionalized 1,1-disubstituted alkenes to access chiral alkanes with full conversion and excellent ee. A novel chiral 8-oxazoline iminoquinoline ligand and its iron complex have been designed and synthesized. This protocol is operationally simple by using 1 atm of hydrogen gas and shows good functional group tolerance. A primary mechanism has been proposed by the deuterium-labeling experiments.
- Lu, Dongpo,Lu, Peng,Lu, Zhan,Ren, Xiang,Sun, Yufeng,Xu, Haofeng
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supporting information
p. 12433 - 12438
(2021/08/23)
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- Method for preparing chiral alkyl compound by catalyzing asymmetric hydrogenation reaction of olefin with iron complex catalyst
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The invention discloses a method for preparing a chiral alkyl compound by catalyzing asymmetric hydrogenation reaction of olefin with an iron complex catalyst, which comprises the steps of by taking disubstituted olefin as shown in a formula I defined in
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Paragraph 0084-0089; 0102-0104; 0151-0155
(2021/05/29)
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- Method for preparing chiral alkyl compound through asymmetric catalytic hydrogenation of E/Z mixed or single-configuration trisubstituted olefin
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The invention discloses a method for preparing a chiral alkyl compound through asymmetric catalytic hydrogenation of an E/Z mixed or single-configuration trisubstituted olefin. The method comprises following steps: taking a trisubstituted olefin represent
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Paragraph 0066-0068; 0090-092
(2020/01/14)
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- Tandem Peterson olefination and chemoselective asymmetric hydrogenation of β-hydroxy silanes
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Here, we report the first Ir-N,P complex catalyzed tandem Peterson olefination and asymmetric hydrogenation of β-hydroxy silanes. This reaction resulted in the formation of chiral alkanes in high isolated yields (up to 99%) and excellent enantioselectivity (up to 99% ee) under mild conditions. Modification of the reaction conditions provides a choice to transform either an olefin or the β-hydroxy silane in a chemoselective manner. Additionally, based on this method, an expedient enantioselective synthesis of (S)-(+)-α-curcumene, from a simple ketone, was accomplished in two steps with 75% overall yield and 95% ee.
- Krajangsri, Suppachai,Wu, Haibo,Liu, Jianguo,Rabten, Wangchuk,Singh, Thishana,Andersson, Pher G.
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p. 3649 - 3653
(2019/03/28)
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- Bioinspired Metal-Free Formal Decarbonylation of α-Branched Aliphatic Aldehydes at Ambient Temperature
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A sequence of a Baeyer–Villiger oxidation and a Lewis acid-promoted reduction of the resulting formate with Et3SiH enabled the metal-free formal decarbonylation of tertiary and secondary aliphatic aldehydes. The new methodology mimics the biosynthetic decarbonylation pathway through oxidative C?C bond cleavage rather than the C(O)?H bond activation known from conventional Tsuji–Wilkinson-type reactions. The substrate scope is complementary to existing transition-metal-catalyzed protocols.
- Richter, Sven C.,Oestreich, Martin
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p. 8508 - 8512
(2019/06/04)
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- Water and Sodium Chloride: Essential Ingredients for Robust and Fast Pd-Catalysed Cross-Coupling Reactions between Organolithium Reagents and (Hetero)aryl Halides
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Direct palladium-catalysed cross-couplings between organolithium reagents and (hetero)aryl halides (Br, Cl) proceed fast, cleanly and selectively at room temperature in air, with water as the only reaction medium and in the presence of NaCl as a cheap additive. Under optimised reaction conditions, a water-accelerated catalysis is responsible for furnishing C(sp3)–C(sp2), C(sp2)–C(sp2), and C(sp)–C(sp2) cross-coupled products, in competition with protonolysis, within a reaction time of 20 s, in yields of up to 99 %, and in the absence of undesired dehalogenated/homocoupling side products even when challenging secondary organolithiums serve as the starting material. It is worth noting that the proposed protocol is scalable and the catalyst and water can easily and successfully be recycled up to 10 times, with an E-factor as low as 7.35.
- Dilauro, Giuseppe,Quivelli, Andrea Francesca,Vitale, Paola,Capriati, Vito,Perna, Filippo Maria
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supporting information
p. 1799 - 1802
(2019/01/25)
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- Asymmetric hydrogenation of α-ethylstyrenes catalyzed by chiral ruthenium complexes
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A combined system of RuCl2[(R,R)-Me-DuPhos](dmf)(n) and t-C4H9OK catalyzes the asymmetric hydrogenation of α-ethylstyrene derivatives. The reaction proceeds with a substrate to catalyst molar ratio of up to 2600 in 2-propanol at 8 atm and room temperature to give the chiral saturated products in 81-89% ee. (C) 2000 Elsevier Science Ltd.
- Forman,Ohkuma,Hems,Noyori
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p. 9471 - 9475
(2007/10/03)
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- Zirconocene-catalyzed alkylation of aryl alkenes with alkyl tosylates, sulfates and bromides
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Styrenes were alkylated with alkyl tosylates, sulfates and bromides in the presence of a zirconocene catalyst and (n)BuMgCl in THF. By the use of this reaction, primary and secondary alkyl groups can be introduced regioselectively at the benzylic carbon of styrenes to give α-substituted ethylbenzenes.
- Terao, Jun,Watanabe, Tsunenori,Saito, Koyu,Kambe, Nobuaki,Sonoda, Noboru
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p. 9201 - 9204
(2007/10/03)
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