66977-67-1Relevant academic research and scientific papers
Method for preparing spiro beta-lactam
-
Paragraph 0052-0054; 0059, (2020/07/12)
The invention discloses a method for preparing spiro beta-lactam. The method comprises the following step: carrying out [2+1] cyclization reaction on beta-lactam and keto ester under the condition ofa phosphine catalyst to generate spiro beta-lactam. The
Synthesis of β-Lactams via Enantioselective Allylation of Anilines with Morita-Baylis-Hillman Carbonates
Krieck, Sven,Lange, Markus,Schüler, Philipp,Vilotijevic, Ivan,Westerhausen, Matthias,Zi, You
, p. 575 - 580 (2020/03/27)
Enantioenriched β-lactams are accessed via enantioselective allylation of anilines with Morita-Baylis-Hillman carbonates followed by a base-promoted cyclization. The resulting 3-methyleneazetidin-2-ones are amenable to diastereoselective functionalization
Organocatalytic Allylic Amination of Morita-Baylis-Hillman Carbonates
Formánek, Bed?ich,?imek, Michal,Kamlar, Martin,Císa?ová, Ivana,Vesely, Jan
, p. 907 - 920 (2019/02/10)
An organocatalytic asymmetric allylic amination of Morita-Baylis-Hillman carbonates with aromatic amines in the presence of β-isocupreidine is described. Chiral allylic amines were obtained in almost quantitative yields (90-96%) with moderate enantioselectivity. Recrystallization afforded products in good yields (45-73%) and high optical purity (82-99% ee). This method provides a facile and efficient route to obtain optically active β-lactams, including the building block of the cholesterol-lowering drug Ezetimibe.
Decarboxylative Organocatalytic Allylic Amination of Morita–Baylis–Hillman Carbamates
Do?ekal, Vojtěch,?imek, Michal,Dra?ínsky, Martin,Vesely, Jan
, p. 13441 - 13445 (2018/09/21)
The present study reports the organocatalytic enantioselective allylic amination of Morita–Baylis–Hillman carbamates efficiently catalyzed by a chiral amine in the presence of a Br?nsted acid. Chiral allylic amines were produced in high yields (up to 98 %) and enantioselectivities (up to 97 % ee). This method provides an efficient and easily performed route to prepare α-methylene-β-lactams, and other optically active β-lactams, such as the cholesterol-lowering drug Ezetimibe.
Design, synthesis, biological evaluation and cocrystal structures with tubulin of chiral β-lactam bridged combretastatin A-4 analogues as potent antitumor agents
Zhou, Pengfei,Liang, Yuru,Zhang, Hao,Jiang, Hao,Feng, Kechang,Xu, Pan,Wang, Jie,Wang, Xiaoming,Ding, Kuiling,Luo, Cheng,Liu, Mingming,Wang, Yang
, p. 817 - 842 (2018/01/10)
A diverse of chiral β-lactam bridged analogues of combretastatin A-4 (CA-4), 3-substituted 1,4-diaryl-2-azetidinones, were asymmetrically synthesized and biologically evaluated, leading to identify a number of potent anti-proliferative compounds represent
A chiral α - methylene β - lactam compound and its preparation method and application
-
, (2017/12/28)
Disclosed are a chiral alpha-methylene-beta-lactam compound and a preparation method and an application thereof. An asymmetric allyl amination reaction of catalyzing a class of Morita-Baylis-Hillman adducts by using a complex formed by a chiral phosphine
Stereoselective Synthesis of Ezetimibe via Cross-Metathesis of Homoallylalcohols and α-Methylidene-β-Lactams
Humpl, Marek,Tauchman, Ji?í,Topolov?an, Nikola,Kretschmer, Jan,Hessler, Filip,Císa?ová, Ivana,Kotora, Martin,Vesely, Jan
, p. 7692 - 7699 (2016/09/09)
Ru-catalyzed cross-metathesis (CM) reaction between β-arylated α-methylidene-β-lactams and terminal olefins was developed. The CM reaction is effectively catalyzed with Hoveyda-Grubbs second-generation catalyst affording corresponding α-alkylidene-β-aryl-
A simple and direct synthesis of 3-methylene-1, 4-diarylazetidin-2-ones and (E)-3-arylidene-1-phenylazetidin-2-ones using baylis-hillman derivatives
Bakthadoss, Manickam,Srinivasan, Jayakumar,Selvakumar, Raman
, p. 295 - 301 (2014/03/21)
Herein we describe a direct method, promoted by potassium tert-butoxide (KOtBu), for the synthesis of highly substituted α-methylene β-lactams and α-arylidene β-lactams from the amino ester intermediates derived from the acetates and bromo derivatives of
Aromatic spiroketal bisphosphine ligands: Palladium-catalyzed asymmetric allylic amination of racemic Morita-Baylis-Hillman adducts
Wang, Xiaoming,Meng, Fanye,Wang, Yan,Han, Zhaobin,Chen, Yong-Jun,Liu, Li,Wang, Zheng,Ding, Kuiling
, p. 9276 - 9282 (2012/10/29)
Showing a backbone: The spiroketal backbone of the bis(phosphine) ligand 1 led to good regio- and enantioselectivity in the palladium-catalyzed asymmetric allylic amination of racemic Morita-Baylis-Hillman adducts with aromatic amines. The methodology provides a facile and efficient synthesis of precursors for optically active β-lactam derivatives, including the cholesterol drug Ezetimibe.
Synthesis of β-amino esters by regioselective amination of allyl bromides with aryl and alkyl amines
Chen, Hung-Yang,Patkar, Laxmikant N.,Ueng, Shau-Hua,Lin, Chun-Cheng,Lee, Adam Shih-Yuan
, p. 2035 - 2038 (2007/10/03)
One of the two possible regioisomers can be exclusively formed by combining a suitable solvent and a specific amount of triethylamine as a base during the amination of allyl bromide 5. The SN2′ product 7 was produced using dichloromethane as a
