57147-21-4Relevant academic research and scientific papers
Electroselective and Controlled Reduction of Cyclic Imides to Hydroxylactams and Lactams
Bai, Ya,Shi, Lingling,Zheng, Lianyou,Ning, Shulin,Che, Xin,Zhang, Zhuoqi,Xiang, Jinbao
, p. 2298 - 2302 (2021/04/05)
An efficient and practical electrochemical method for selective reduction of cyclic imides has been developed using a simple undivided cell with carbon electrodes at room temperature. The reaction provides a useful strategy for the rapid synthesis of hydroxylactams and lactams in a controllable manner, which is tuned by electric current and reaction time, and exhibits broad substrate scope and high functional group tolerance even to reduction-sensitive moieties. Initial mechanistic studies suggest that the approach heavily relies on the utilization of amines (e.g., i-Pr2NH), which are able to generate α-aminoalkyl radicals. This protocol provides an efficient route for the cleavage of C-O bonds under mild conditions with high chemoselectivity.
Chemoselective Electrosynthesis Using Rapid Alternating Polarity
Baran, Phil S.,Carlson, Ethan,Edwards, Jacob T.,Hayashi, Kyohei,Kawamata, Yu,Saito, Masato,Shaji, Shobin,Simmons, Bryan J.,Waldmann, Dirk,Zapf, Christoph W.
supporting information, p. 16580 - 16588 (2021/10/20)
Challenges in the selective manipulation of functional groups (chemoselectivity) in organic synthesis have historically been overcome either by using reagents/catalysts that tunably interact with a substrate or through modification to shield undesired sites of reactivity (protecting groups). Although electrochemistry offers precise redox control to achieve unique chemoselectivity, this approach often becomes challenging in the presence of multiple redox-active functionalities. Historically, electrosynthesis has been performed almost solely by using direct current (DC). In contrast, applying alternating current (AC) has been known to change reaction outcomes considerably on an analytical scale but has rarely been strategically exploited for use in complex preparative organic synthesis. Here we show how a square waveform employed to deliver electric current - rapid alternating polarity (rAP) - enables control over reaction outcomes in the chemoselective reduction of carbonyl compounds, one of the most widely used reaction manifolds. The reactivity observed cannot be recapitulated using DC electrolysis or chemical reagents. The synthetic value brought by this new method for controlling chemoselectivity is vividly demonstrated in the context of classical reactivity problems such as chiral auxiliary removal and cutting-edge medicinal chemistry topics such as the synthesis of PROTACs.
Preparation method of hydroxyl lactam
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Paragraph 0103; 0104; 0105; 0106, (2020/02/19)
The invention discloses a preparation method of hydroxyl lactam. The hydroxyl lactam is prepared from cyclic imide shown in a formula (II) through a homogeneous catalytic hydrogenation reaction, wherein R1, R2 and R3 are respectively and independently H,
Manganese-Catalyzed Desaturation of N-Acyl Amines and Ethers
Li, Gang,Kates, Patrick A.,Dilger, Andrew K.,Cheng, Peter T.,Ewing, William R.,Groves, John T.
, p. 9513 - 9517 (2019/10/14)
Enamines and enol ethers are versatile synthons for chemical synthesis. While several methods have been developed to access such molecules, prefunctionalized starting materials are usually required, and direct desaturation methods remain rare. Herein, we report direct desaturation reactions of N-protected cyclic amines and cyclic ethers using a mild I(III) oxidant, PhI(OAc)2, and an electron-deficient manganese pentafluorophenylporphyrin catalyst, Mn(TPFPP)Cl. This system displays high efficiency for α,β-desaturation of various cyclic amines and ethers. Mechanistic probes suggest that the desaturation reaction occurs via an initial α-C-H hydroxylation pathway, which serves to protect the product from overoxidation.
Stereoselective cycloaddition of N-acyliminium ions with α,β-unsaturated ketones and esters
Qian, Lingfeng,Zhou, Yuehua,Zhang, Wei
experimental part, p. 449 - 456 (2010/10/20)
The [4+2] reactions of N-acyliminium ions, produced from 2-aryl-3-hydroxy-2,3-dihydroisoindol-1-onesor5-hydroxy-1-phenyl-2,5-dihydro/2,3,4,5-tetrahydropyrrol-2-ones in the presence of BF3OEt2, with α,β-unsaturated ketones or esters w
A concise synthesis of pyrrolo- and pyrrolidino[1,2-a]quinolin-1-ones via Diels-Alder reactions of N-acyliminium cations with olefins
Zhang, Wei,Huang, Limin,Wang, Junpu
, p. 2053 - 2063 (2007/10/03)
A concise and efficient synthesis of pyrrolo- and pyrrolidino[1,2-a] quinolin-1-ones has been developed. New members of this family can thus be generated via Diels-Alder reactions of olefins with N-acyliminium cations produced, in the presence of BF3
