32587-80-7Relevant academic research and scientific papers
Copper-catalyzed enantioselective conjugate addition of Grignard reagents to acyclic enones
Lopez, Fernando,Harutyunyan, Syuzanna R.,Minnaard, Adriaan J.,Feringa, Ben L.
, p. 12784 - 12785 (2004)
A highly enantioselective Cu-catalyzed addition of Grignard reagents to acyclic aliphatic enones is described. In the presence of 5 mol % of CuBr·SMe2 and 6 mol % of JosiPhos diphosphine aliphatic enones react with Grignard reagents to provide β-substituted linear ketones with high yields, regio-, and enantioselectivities. Copyright
1,1'-binaphthalene-8,8'-diol as en efficient chiral controller: Highly enantioselective synthesis of optically active ketones
Fuji, Kaoru,Yang, Xiao-Shen,Tanaka, Kiyoshi,Asakawa, Naoyuki,Hao, Xiao-Jian
, p. 7373 - 7376 (1996)
Half esters (R)-5 of 1,1'-binaphthalene-8,8'-diol undergo 1,4-addition of lithium dialkyl cuprates followed by formal 1,2-addition to give β-substituted ketones (S)-6 or (S)-7 with high enantioselectivity (96 ~ 100% ee). A brief discussion of the mechanis
Successive 1,4- and 1,2-additions of organometallic reagents to a chiral binaphthyl ester: One step synthesis of optically active ketones
Fuji,Tanaka,Mizuchi,Hosoi
, p. 7277 - 7280 (1991)
Organometallic reagents undergo a 1,4-addition onto the chiral binaphthyl ester of α,β-unsaturated carboxylic acid followed by the formal 1,2-addition to yield optically active ketones directly.
Cobalt-Catalyzed Asymmetric 1,4-Hydroboration of Enones with HBpin
Ren, Xiang,Lu, Zhan
, p. 8370 - 8374 (2021/11/01)
Herein, a series of new 8-OIQ cobalt complexes were synthesized and used for cobalt-catalyzed chemo- and enantioselective 1,4-hydroboration of enones with HBpin to access chiral β,β-disubstituted ketones with good to excellent chemo- and enantioselectivties. This protocol is operationally simple and shows a broad substrate scope.
Chiral-Anion-Mediated Asymmetric Heck-Matsuda Reaction of Acyclic Alkenyl Alcohols
Zhang, Tao,Li, Wen-Ao,Shen, Hong-Cheng,Chen, Shu-Sen,Han, Zhi-Yong
supporting information, p. 1473 - 1477 (2021/03/08)
Acyclic internal alkenes are a class of challenging substrates in asymmetric Heck-type reactions due to difficulties related to both reactivity and selectivity control. Employing acyclic alkenyl alcohols, an asymmetric Heck-Matsuda reaction is developed through the strategy of chiral anion phase transfer. Various chiral ketones could be obtained in high levels of enantioselectivity. A catalytic amount of dimethyl sulfoxide (DMSO) as an additive is crucial for the reaction to suppress the palladium-hydride-mediated side reactions.
Highly Enantioselective Iridium-Catalyzed Hydrogenation of Conjugated Trisubstituted Enones
Peters, Bram B. C.,Jongcharoenkamol, Jira,Krajangsri, Suppachai,Andersson, Pher G.
supporting information, p. 242 - 246 (2021/01/13)
Asymmetric hydrogenation of conjugated enones is one of the most efficient and straightforward methods to prepare optically active ketones. In this study, chiral bidentate Ir-N,P complexes were utilized to access these scaffolds for ketones bearing the stereogenic center at both the α- and β-positions. Excellent enantiomeric excesses, of up to 99%, were obtained, accompanied with good to high isolated yields. Challenging dialkyl substituted substrates, which are difficult to hydrogenate with satisfactory chiral induction, were hydrogenated in a highly enantioselective fashion.
Asymmetric Umpolung Hydrogenation and Deuteration of Alkenes Catalyzed by Nickel
Guo, Siyu,Wang, Xiuhua,Zhou, Jianrong Steve
supporting information, p. 1204 - 1207 (2020/02/04)
Nickel-catalyzed asymmetric hydrogenation of several types of alkenes proceeds in high enantioselectivity, using acetic acid or water as the hydrogen source and indium powder as electron donor. The scope of alkenes herein include α,β-unsaturated esters, n
Heterogeneous Rh and Rh/Ag bimetallic nanoparticle catalysts immobilized on chiral polymers
Min, Hyemin,Miyamura, Hiroyuki,Yasukawa, Tomohiro,Kobayashi, Shu
, p. 7619 - 7626 (2019/08/20)
The development of heterogeneous chiral catalysts has lagged far behind that of homogeneous chiral catalysts in spite of their advantages, such as environmental friendliness for a sustainable society. We describe herein novel heterogeneous chiral Rh and Rh/Ag bimetallic nanoparticle catalysts consisting of polystyrene-based polymers with chiral diene moieties. The catalysts enable high-to-excellent yields and enantioselectivities to be obtained in asymmetric 1,4-addition reactions of arylboronic acids with α,β-unsaturated carbonyl compounds such as ketones, esters, and amides, and in other asymmetric reactions. The catalysts could be readily recovered by simple filtration and reused; they could also be applied to continuous-flow synthesis. We also discuss the nature of possible reaction species based on XPS analysis.
In Situ Generated Gold Nanoparticles on Active Carbon as Reusable Highly Efficient Catalysts for a Csp3 ?Csp3 Stille Coupling
Holz, Julia,Pfeffer, Camilla,Zuo, Hualiang,Beierlein, Dennis,Richter, Gunther,Klemm, Elias,Peters, René
supporting information, p. 10330 - 10334 (2019/06/27)
Gold nanoparticle catalysts are important in many industrial production processes. Nevertheless, for traditional Csp2-Csp2 cross-coupling reactions they have been rarely used and Pd catalysts usually give a superior performance. Herein we report that in situ formed gold metal nanoparticles are highly active catalysts for the cross coupling of allylstannanes and activated alkylbromides to form Csp3-Csp3 bonds. Turnover numbers up to 29 000 could be achieved in the presence of active carbon as solid support, which allowed for convenient catalyst recovery and reuse. The present study is a rare case where a gold metal catalyst is superior to Pd catalysts in a cross-coupling reaction of an organic halide and an organometallic reagent.
Chiral 1,3,2-Diazaphospholenes as Catalytic Molecular Hydrides for Enantioselective Conjugate Reductions
Miaskiewicz, Solène,Reed, John H.,Donets, Pavel A.,Oliveira, Caio C.,Cramer, Nicolai
supporting information, p. 4039 - 4042 (2018/03/13)
Secondary 1,3,2-diazaphospholenes have a polarized P?H bond and are emerging as molecular hydrides. Herein, a class of chiral, conformationally restricted methoxy-1,3,2-diazaphospholene catalysts is reported. We demonstrate their catalytic potential in asymmetric 1,4-reductions of α,β-unsaturated carbonyl derivatives, including enones, acyl pyrroles, and amides, which proceeded in enantioselectivities of up to 95.5:4.5 e.r.
