238091-03-7Relevant academic research and scientific papers
Catalytic enantioselective Nozaki-Hiyama allylation reaction with tethered bis(8-quinolinolato) (TBOx) chromium complex
Xia, Guoyao,Yamamoto, Hisashi
, p. 2554 - 2555 (2006)
The utility of the new class of chiral ligand, tethered bis(8-quinolinol) (TBOxH), is further explored. Its chromium complex, TBOxCr(III)Cl, effectively catalyzes the Nozaki-Hiyama allylation reactions of various aldehydes at room temperature with high yield (up to 95%) and high enantioselectivity (up to 99% ee). The scope of the present method is shown to be wide, and this method represents an efficient access to chiral homoallylic alcohols. Copyright
A chiral oxazoline for catalytic enantioselective Nozaki-Hiyama-Kishi allylation and vinylation of aldehydes
Chen, Chinpiao,Kumbhar, Sharad V.
, (2020/09/22)
Asymmetric allylation and vinylation of aldehydes with allyl halides and vinyl halides have been achieved using the chromium(II)-oxazoline catalyst. The catalyst promotes the highly efficient enantioselective Nozaki–Hiyama-Kishi (NHK) allylation of aldehydes using allyl bromide, producing the corresponding homoallylic alcohols in good yields (up to 84%) and a high level of enantioselectivity (up to 98% ee). Meanwhile, the NHK vinylation of aldehydes produce desired allylic alcohols in satisfactory yields (up to 88%) and a high level of enantioselectivity (up to 97% ee). We developed a reliable and milder protocol for preparing chiral homoallylic and allylic alcohols.
Bi(cyclopentyl)diol-Derived Boronates in Highly Enantioselective Chiral Phosphoric Acid-Catalyzed Allylation, Propargylation, and Crotylation of Aldehydes
Yuan, Jinping,Jain, Pankaj,Antilla, Jon C.
, p. 12988 - 13003 (2020/11/23)
In this study, we disclose the catalytic addition of bi(cyclopentyl)diol-derived boronates to aldehydes promoted by chiral phosphoric acids, allowing for the formation of enantioenriched homoallylic, propargylic, and crotylic alcohols (up to >99% enantiom
Hollow organic polymeric nano-bowls-supported BINOL-derived chiral phosphoric acid: enhanced catalytic performances in the enantioselective allylation of aromatic aldehydes
Yan, Zhengwei,Xie, Guangxin,Zhang, Jianing,Ma, Xuebing
, p. 39 - 47 (2019/01/04)
To improve the catalytic efficiency of expensive and versatile 1, 1′-binaphthol-derived chiral phosphoric acid with 2, 4, 6-tris(isopropyl)phenyl substituents and mass transfer of reactants in heterogeneous catalysis, a hollow organic polymeric nano-bowl
Asymmetric Allylation of Carbonyl Compounds Catalyzed by a Chiral Phosphine–Silver Complex
Yanagisawa, Akira,Yang, Nan,Bamba, Kentaro
supporting information, p. 6614 - 6618 (2017/12/15)
A catalytic, asymmetric allylation reaction of aldehydes or ketones with allyltrimethoxysilane was achieved by using a BINAP·AgBF4 [BINAP = 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl] complex as the chiral precatalyst and triethylamine as the
Enantioselective Allyl-, and Allenylboration of Aldehydes Catalyzed by Chiral Hydroxyl Carboxylic Acid
Ota, Yuya,Kawato, Yuji,Egami, Hiromichi,Hamashima, Yoshitaka
supporting information, p. 976 - 980 (2017/05/05)
Asymmetric allylboration of aldehydes with allylboronic acid pinacol ester catalyzed by chiral hydroxyl carboxylic acid is described. This reaction provides synthetically useful homoallyl alcohols in high yield with good to high enantioselectivity. The pr
Polystyrene-Supported TRIP: A highly recyclable catalyst for batch and flow enantioselective allylation of aldehydes
Clot-Almenara, Lidia,Rodríguez-Escrich, Carles,Osorio-Planes, Laura,Pericas, Miquel A.
, p. 7647 - 7651 (2018/05/23)
The widely applicable TRIP phosphoric acid catalyst has been immobilized on polystyrene using a copolymerization-based strategy. The resin (PS-TRIP) has proven to be highly active and enantioselective in the asymmetric allylboration of aldehydes. Moreover
Practical, highly stereoselective allyl- and crotylsilylation of aldehydes catalyzed by readily available Cinchona alkaloid amide
Huang, Yuan,Yang, Licheng,Shao, Panlin,Zhao, Yu
, p. 3275 - 3281 (2013/07/26)
We have demonstrated that bidentate Lewis base catalysts can be constructed based on the Cinchona alkaloid structure that promote highly stereoselective reactions of allyl- and crotyltrichlorosilane with aromatic as well as aliphatic aldehydes (90-99% ee, >98% diastereoselectivity). The catalysts are available in a one-pot procedure in >70% yield from cheap starting materials and promote the allylation reactions at ambient temperature. Gram scale reactions with catalyst recovery and reuse showcased the practicality of the catalytic system.
Synthetically amenable amide derivatives of tosylated-amino acids as organocatalysts for enantioselective allylation of aldehydes: Computational rationale for enantioselectivity
Ghosh, Debashis,Sahu, Debashis,Saravanan,Abdi, Sayed H. R.,Ganguly, Bishwajit,Khan, Noor-Ul H.,Kureshy, Rukhsana I.,Bajaj, Hari C.
supporting information, p. 3451 - 3460 (2013/06/05)
A phenylalanine derived chiral amide is developed that serves as an effective organocatalyst for the reaction of allyltrichlorosilane with aryl, hetero-aryl and α,β-unsaturated aldehydes to afford the desired homoallylic alcohols in good yield (up to 90%)
Asymmetric synthesis of novel axially chiral 2,2′-bipyridine n,n′-dioxides bearing α-amino acid residues and their applications in enantioselective allylation of aromatic aldehydes with allyltrichlorosilane
Zhao, Hongwu,Yue, Yuanyuan,Li, Hailong,Sheng, Zhihui,Yang, Zhao,Meng, Wei
, p. 485 - 493 (2013/08/25)
A series of novel axially chiral 2,2′-bipyridine N,N′-dioxides bearing C1 or C2-symmetry have been synthesized by the use of enantiopure α-amino acids as chiral sources. The absolute stereochemistry of the axial chirality of these or
