204334-88-3Relevant academic research and scientific papers
Temperature and ultrasound rate enhancement in the Baylis-Hillman reaction
Roos,Rampersadh
, p. 1261 - 1266 (1993)
Synthetically useful increases in reaction rate are achieved in the DABCO (1,4-diazabicyclo [2.2.2] octane) catalysed coupling of aldehydes with methyl acrylate by the application of ultrasound.
Strain-Driven Dyotropic Rearrangement: A Unified Ring-Expansion Approach to α-Methylene-γ-butyrolactones
Lei, Xiaoqiang,Li, Yuanhe,Lai, Yang,Hu, Shengkun,Qi, Chen,Wang, Gelin,Tang, Yefeng
supporting information, p. 4221 - 4230 (2020/12/22)
An unprecedented strain-driven dyotropic rearrangement of α-methylene-β-lactones has been realized, which enables the efficient access of a wide range of α-methylene-γ-butyrolactones displaying remarkable structural diversity. Several appealing features of the reaction, including excellent efficiency, high stereospecificity, predictable chemoselectivity and broad substrate scope, render it a powerful tool for the synthesis of MBL-containing molecules of either natural or synthetic origin. Both experimental and computational evidences suggest that the new variant of dyotropic rearrangements proceed in a dualistic pattern: while an asynchronous concerted mechanism most likely accounts for the reactions featuring hydrogen migration, a stepwise process involving a phenonium ion intermediate is favored in the cases of aryl migration. The great synthetic potential of the title reaction is exemplified by its application to the efficient construction of several natural products and relevant scaffolds.
Modular and Stereoselective Approach to Highly Substituted Indole/Pyrrole-Fused Diazepanones
Wang, Shutao,Wang, Siyu,Song, Shaoli,Gao, Qiansong,Wen, Chunxi,Zhang, Zhuoqi,Zheng, Lianyou,Xiang, Jinbao
, p. 6458 - 6466 (2021/05/29)
A one-pot synthetic method for indole/pyrrole-fused 1,4-diazepanone scaffolds has been developed. This method involves a sequential amide coupling/intramolecular aza-Michael addition of 1H-indole/pyrrole-2-carboxylic acids with Morita-Baylis-Hillman-deriv
Enantioselective Lewis base catalyzed phosphonyldifluoromethylation of allylic fluorides using a: C -silyl latent pronucleophile
Zi, You,Lange, Markus,Vilotijevic, Ivan
supporting information, p. 5689 - 5692 (2020/06/19)
The first enantioselective phosphonyldifluoromethylation is enabled by the use of diethyl (difluoro(trimethylsilyl)-methyl)phosphonate reagent as a latent pronucleophile in the Lewis base catalyzed substitution of allylic fluorides. The reaction proceeds
β,γ-Diaryl α-methylene-γ-butyrolactones as potent antibacterials against methicillin-resistant Staphylococcus aureus
Abutaleb, Nader S.,Hamann, Henry J.,Pal, Rusha,Ramachandran, P. Veeraraghavan,Seleem, Mohamed N.
supporting information, (2020/10/02)
A selected series of racemic α-methylene-γ-butyrolactones (AMGBL) synthesized via allylboration or allylindation reactions were screened against methicillin-resistant Staphylococcus aureus (MRSA) USA300. Unlike natural AMGBLs, such as parthenolide, synthe
Latent Nucleophiles in Lewis Base Catalyzed Enantioselective N-Allylations of N-Heterocycles
Zi, You,Lange, Markus,Schultz, Constanze,Vilotijevic, Ivan
supporting information, p. 10727 - 10731 (2019/07/09)
Latent nucleophiles are compounds that are themselves not nucleophilic but can produce a strong nucleophile when activated. Such nucleophiles can expand the scope of Lewis base catalyzed reactions. As a proof of concept, we report that N-silyl pyrroles, i
Direct Activation of Unmodified Morita-Baylis-Hillman Alcohols through Phosphine Catalysis for Rapid Construction of Three-Dimensional Heterocyclic Compounds
Zhou, Leijie,Yuan, Chunhao,Zeng, Yuan,Wang, Qijun,Wang, Chang,Liu, Min,Wang, Wei,Wu, Yongjun,Zheng, Bing,Guo, Hongchao
supporting information, p. 4882 - 4886 (2019/06/27)
The phosphine-catalyzed tandem annulation reaction of Morita-Baylis-Hillman (MBH) alcohols with azomethine imines has been achieved for the synthesis of biologically important (epoxymethano)-pyrazolo[5,1-b]quinazoline derivatives. A variety of MBH alcohol
Copper-Catalyzed One-Pot Borylative Aldolisation β-Fluoride Elimination for the Formal Addition of Acrylates to Carbonyl Moieties
Rasson, Corentin,Stouse, Adrien,Boreux, Arnaud,Cirriez, Virginie,Riant, Olivier
, p. 9234 - 9237 (2018/06/04)
Herein, we report the copper-catalyzed domino borylation/aldolisation of methyl 2-fluoroacrylate with carbonyl compounds followed by an elimination to give Morita–Baylis–Hillman (MBH) analogues. The optimal conditions described were shown to be compatible
2 H-Chromene-3-carboxylic Acid Synthesis via Solvent-Controlled and Rhodium(III)-Catalyzed Redox-Neutral C-H Activation/[3 + 3] Annulation Cascade
Zhou, Zhi,Bian, Mengyao,Zhao, Lixin,Gao, Hui,Huang, Junjun,Liu, Xiawen,Yu, Xiyong,Li, Xingwei,Yi, Wei
supporting information, p. 3892 - 3896 (2018/07/22)
An efficient and redox-neutral synthesis of 2H-chromene-3-carboxylic acids from N-phenoxyacetamides and methyleneoxetanones has been realized via a solvent-controlled and rhodium(III)-catalyzed C-H activation/unusual [3 + 3] annulation sequence. This tran
A cascade synthesis of: S -allyl benzoylcarbamothioates via Mumm-type rearrangement
Dahiya, Anjali,Ali, Wajid,Alam, Tipu,Patel, Bhisma K.
supporting information, p. 7787 - 7791 (2018/11/21)
A catalyst and solvent free synthesis of S-allyl benzoylcarbamothioates has been achieved from the in situ generated benzoylcarbonimidothioates obtained by reacting MBH alcohols with aroyl isothiocyanates. An intramolecular thia-Michael addition of the in
