69897-46-7Relevant academic research and scientific papers
Enantioselective Mukaiyama-aldol and aldol-dihydropyrone annulation reactions catalyzed by a tryptophan-derived oxazaborolidine
Corey,Cywin, Charles L.,Roper, Thomas D.
, p. 6907 - 6910 (1992)
The (S)-tryptophan derived catalyst 1, has been used to effect enantioselective Mukaiyama-aldol and aldol-dihydropyrone annulation reactions of trimethylsilyloxy olefins and dienes.
Chiral Bipyridine Ligand with Flexible Molecular Recognition Site: Development and Application to Copper-Catalyzed Asymmetric Borylation of α,β-Unsaturated Ketones
Tsutsumi, Ryosuke,Taguchi, Rika,Yamanaka, Masahiro
, (2021/10/20)
A novel chiral bipyridine ligand bearing a flexible side chain with a molecular recognition site enables precise stereocontrol through the cooperative action of metal center and hydrogen bonds. This new chiral ligand was applied to the copper-catalyzed as
Cellulosic CuI Nanoparticles as a Heterogeneous, Recyclable Catalyst for the Borylation of α,β-Unsaturated Acceptors in Aqueous Media
Zhou, Lijie,Han, Biao,Zhang, Yaoyao,Li, Bojie,Wang, Liansheng,Wang, Jianying,Wang, Xianbao,Zhu, Lei
, p. 3220 - 3229 (2021/03/06)
Abstract: We have demonstrated that cellulosic CuI nanoparticles could perform as an efficient heterogeneous catalyst for the synthesis of useful organoboron compounds. Desired β-borylation products were all obtained in good to excellent yields under mild
1,3 - Diphenyl -1 - propanol and preparation method thereof
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Paragraph 0063; 0072-0074, (2020/11/11)
The invention relates to 1, 3-diphenyl-1-propanol and a preparation method thereof and belongs to the technical field of chemical synthesis. The preparation method comprises that benzaldehyde and acetophenone undergo a catalytic reaction in the presence of dibenzylamine trifluoroacetate and a catalyst to produce 3-hydroxy-1, 3-diphenyl-1-propanone, and the 3-hydroxy-1, 3-diphenyl-1-propanone undergoes a Huang Minglon reduction reaction to produce 1, 3-diphenyl-1-propanol, wherein the catalyst is L-proline or D-proline. The preparation method has simple processes, realizes a low cost and prepares an optically pure product satisfying the requirements. The invention also relates to 1, 3-diphenyl-1-propanol obtained by the preparation method.
Kinetic Resolution of β-Hydroxy Carbonyl Compounds via Enantioselective Dehydration Using a Cation-Binding Catalyst: Facile Access to Enantiopure Chiral Aldols
Paladhi, Sushovan,Hwang, In-Soo,Yoo, Eun Jeong,Ryu, Do Hyun,Song, Choong Eui
supporting information, p. 2003 - 2006 (2018/04/16)
A practical and highly enantioselective nonenzymatic kinetic resolution of racemic β-hydroxy carbonyl (aldol) compounds through enantioselective dehydration process was developed using a cation-binding Song's oligoethylene glycol (oligoEG) catalyst with p
Cascade Reaction by Chemo- and Biocatalytic Approaches to Obtain Chiral Hydroxy Ketones and anti 1,3-Diols
Gandolfi, Raffaella,Facchetti, Giorgio,Christodoulou, Michael S.,Fusè, Marco,Meneghetti, Fiorella,Rimoldi, Isabella
, p. 393 - 400 (2018/06/04)
A chemo- and biocatalytic cascade approach was applied for the stereoselective synthesis of hydroxy ketones and the corresponding 1,3-diols. A new class of tridentate N,N,O ligands was used with copper(II) complexes for the asymmetric β-borylation of α,β-unsaturated compounds. The complex containing ligand L5 emerged as the best performer, and it gave the organoborane derivatives with good ee values. The corresponding keto–alcohol compounds were then bioreduced by yeasts. The biotransformation set up with Rhodotorula rubra allowed (R)-keto–alcohols and (S,S)-diols to be obtained with up to 99 % ee and up to 99 % de in favor of the anti enantiomers.
Direct asymmetric aldol reaction of acetophenones with aromatic aldehydes catalyzed by chiral Al/Zn heterobimetallic compounds
Li, Xiao,Zhang, Lei,Xiao, Yu-Hua,Guo, Qi-Peng,Da, Chao-Shan,Li, Hong,Liu, Xiaoju,Ma, Xiangrong,Ma, Yajun
, p. 1922 - 1930 (2016/10/04)
Chiral Al/Zn heterobimetallic complexes are effective catalysts for the direct highly enantioselective aldol reaction of acetophenones with aromatic aldehydes. The Al site in the complex acts as a Lewis acid to activate aldehyde, whereas ethylzinc alkoxide plays a role of a Br?nsted base to form a reactive zinc enolate with acetophenone. Distinct nature of two different metals contributes to the efficient direct asymmetric aldol reaction.
Asymmetric chemoenzymatic synthesis of 1,3-diols and 2,4-disubstituted aryloxetanes by using whole cell biocatalysts
Vitale, Paola,Perna, Filippo Maria,Agrimi, Gennaro,Scilimati, Antonio,Salomone, Antonio,Cardellicchio, Cosimo,Capriati, Vito
supporting information, p. 11438 - 11445 (2016/12/16)
Regio- and stereo-selective reduction of substituted 1,3-aryldiketones, investigated in the presence of different whole cell microorganisms, was found to afford β-hydroxyketones or 1,3-diols in very good yields (up to 95%) and enantiomeric excesses (up to 96%). The enantiomerically enriched aldols, obtained with the opposite stereo-preference by baker's yeast and Lactobacillus reuteri DSM 20016 bioreduction, could then be diastereoselectively transformed into optically active syn- or anti-1,3-diols by a careful choice of the chemical reducing agent (diastereomeric ratio up to 98 : 2). The latter, in turn, were stereospecifically cyclized into the corresponding oxetanes in 43-98% yields and in up to 94% ee, thereby giving a diverse selection of stereo-defined 2,4-disubstituted aryloxetanes.
Regio- and enantioselective reduction of diketones: Preparation of enantiomerically pure hydroxy ketones catalysed by Candida parapsilosis ATCC 7330
Mahajabeen, Pula,Chadha, Anju
, p. 1167 - 1173 (2015/10/28)
Enantiomerically enriched hydroxy ketones were prepared by the reduction of the corresponding diketones with excellent enantiomeric excess (98%) and in good yields (up to 75%) using whole cells of Candida parapsilosis ATCC 7330. Cyclic diketones, such as 1,2-cyclohexanedione and 1,4-cyclohexanedione, resulted in hydroxy ketones as products. Cyclohexane-1,3-dione and 5,5-dimethylcyclohexane-1,3-dione gave dimerised products, such as 2,2′-(ethane-1,1-diyl)bis(3-hydroxycyclohex-2-enone) and 2,2′-(ethane-1,1-diyl)bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) with acetaldehyde generated in situ from whole cells of Candida parapsilosis ATCC 7330, which is reported here for the first time.
Chiral Br?nsted Acid as a True Catalyst: Asymmetric Mukaiyama Aldol and Hosomi-Sakurai Allylation Reactions
Sai, Masahiro,Yamamoto, Hisashi
, p. 7091 - 7094 (2015/06/25)
Highly diastereo- and enantioselective Mukaiyama aldol reaction catalyzed by a new chiral Br?nsted acid, N-(perfluorooctanesulfonyl)thiophosphoramide, is described. The perfluorooctyl substituent on the sulfonyl group of the catalyst plays an essential role in the stereoselection. The catalyst also allows the asymmetric Hosomi-Sakurai allylation, which has been considerably challenging due to the low reactivity of allylsilanes. 29Si and 31P NMR monitoring reveals the characteristic feature of the thiophosphoramide catalyst, acting as a strong Br?nsted acid even in the presence of excess silyl nucleophiles, which cannot be found in other related phosphoric acid analogues.
