7383-19-9Relevant academic research and scientific papers
Synthesis of non-racemic unsymmetrical tetrasubstituted vinylallenes
Spino,Frechette
, p. 8033 - 8036 (2000)
Tetrasubstituted chiral vinylallenes are constructed from the enantioselective epoxidation of an enyne followed by an S(N)2' addition of a cuprate. (C) 2000 Elsevier Science Ltd.
Metal-free synthesis of β-aminoketones by the reductive hydroamination of ynones
Fu, Rui,Liu, Yu,Wu, Tao,Zhang, Xinyu,Zhu, Yang,Luo, Jiangbin,Zhang, Zhengyu,Jiang, Yaojia
supporting information, p. 3525 - 3528 (2022/03/31)
This study describes a cascade method for the synthesis of β-aminoketones through the reductive hydroamination of alkynes under very mild metal-free conditions. It allows for the rapid conversion of ynones and amines into corresponding β-aminoketones with a broad substrate scope and diverse functionalities. This straightforward and easy-to-handle reaction process can be successfully applied for the synthesis of Proroxan and Propipocaine, offering a potential option for the synthesis of drug molecules with the β-aminoketone skeleton.
The Synthesis of Chiral Allyl Carbamates via Merger of Photoredox and Nickel Catalysis
Garbacz, Mateusz,Stecko, Sebastian
supporting information, p. 3213 - 3222 (2020/07/06)
A mild, and versatile, organophotoredox/Ni-mediated protocol was developed for the direct preparation of diverse, enantioenriched allyl carbamates. The reported approach represents a significant departure from classical step-by-step synthesis of allyl carbamates. This dual photoredox/Ni based strategy offers unrivalled capacity for convergent unification of readily available alkyl halides and chiral carbamates derived from 1-bromo-alken-3-ols with high chemoselectivity and efficiency. The reported photoredox/Ni catalyzed cross-coupling reaction is not limited to carbamates, but also to other O-derivatives such as esters, ethers, acetals, carbonates or silyl ethers. To demonstrate the utility of the reported protocol, the resulting allyl carbamates were transformed into functionalized non-racemic allylamines through a sigmatropic rearrangement reaction in enantiospecific manner. This approach allowed for synthesis of enantiomeric allylamines by a simple control of the geometry of a double bond of allyl carbamates. (Figure presented.).
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
supporting information, 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
Ester Synthesis in Water: Mycobacterium smegmatis Acyl Transferase for Kinetic Resolutions
de Leeuw, Nicolas,Torrelo, Guzman,Bisterfeld, Carolin,Resch, Verena,Mestrom, Luuk,Straulino, Emanuele,van der Weel, Laura,Hanefeld, Ulf
, p. 242 - 249 (2017/11/16)
The acyl transferase from Mycobacterium smegmatis (MsAcT) catalyses transesterification reactions in aqueous media because of its hydrophobic active site. Aliphatic cyanohydrin and alkyne esters can be synthesised in water with excellent and strikingly opposite enantioselectivity [(R);E>37 and (S);E>100, respectively]. When using this enzyme, the undesired hydrolysis of the acyl donor is an important factor to take into account. Finally, the choice of acyl donor can significantly influence the obtained enantiomeric excesses. (Figure presented.).
Trialkyl Methanetricarboxylate as Dialkyl Malonate Surrogate in Copper-Catalyzed Enantioselective Propargylic Substitution
Huang, Guanxin,Cheng, Cang,Ge, Luo,Guo, Beibei,Zhao, Long,Wu, Xiaoyu
supporting information, p. 4894 - 4897 (2015/10/12)
The first copper-catalyzed enantioselective propargylation of trialkyl methantricarboxylate with propargylic alcohol derivatives was developed. The tricarboxylate unit in the obtained adducts could be easily transformed into a malonate moiety by treating with in situ generated NaOEt in excellent yield without racemization.
Diastereo- and enantioselective propargylation of benzofuranones catalyzed by pybox-copper complex
Zhao, Long,Huang, Guanxin,Guo, Beibei,Xu, Lijun,Chen, Jie,Cao, Weiguo,Zhao, Gang,Wu, Xiaoyu
supporting information, p. 5584 - 5587 (2015/02/19)
Diastereo- and enantioselective preparation of 2,2-disubstituted benzofuran-3(2H)-one has been realized by a pybox-copper catalyzed reaction between 2-substituted benzofuran-3(2H)-one and propargyl acetate. The utility of this method was demonstrated by further transformation of the terminal alkyne into a methyl ketone without loss of enantiomeric purity.
Chemoenzymatic total synthesis of paecilocin A and 3-butyl-7- hydroxyphthalide
Sreelakshmi, Ch.,Bhaskar Rao,Lakshmi Narasu,Janardhan Reddy,Reddy, B.V. Subba
, p. 1303 - 1305 (2014/03/21)
A highly enantioselective total synthesis of paecilocin A and 3-butyl-7-hydroxyphthalide is described. The key steps involved in this synthesis are enzymatic kinetic resolution and Alder-Rickert reaction.
One-pot deracemization of sec-alcohols: Enantioconvergent enzymatic hydrolysis of alkyl sulfates using stereocomplementary sulfatases
Schober, Markus,Toesch, Michael,Knaus, Tanja,Strohmeier, Gernot A.,Van Loo, Bert,Fuchs, Michael,Hollfelder, Florian,Macheroux, Peter,Faber, Kurt
, p. 3277 - 3279 (2013/04/23)
Hand in hand: The title transformation was achieved using a pair of sulfatases acting through inversion and retention of configuration on opposite substrate enantiomers. Using Pseudomonas aeruginosa arylsulfatase PAS with alkylsulfatase PISA1 in one-pot l
New and efficient synthesis of 1,3-dienylphosphonates by palladium-catalyzed substitution of propargylic esters to diethyl phosphite
Liu, Xiao-Ning,Guo, Wei-Lei,Hou, Chuan-Jin,Hu, Xiang-Ping
supporting information, p. 2622 - 2626 (2013/07/26)
An efficient route to the synthesis of 1,3-dienylphosphonates (1) has been developed for the first time by the substitution of propargylic esters (2) to the diethyl phosphite (3) nucleophile in the presence of Pd2 (dba) 3 · CHCl3 (2 mol %) and 2,2′- bis(diphenylphosphino)-1,1′-binaphthyl (4 mol%). Both the alkyl and aryl 1,3-dienylphosphonates can be prepared from this transformation. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
