1401072-41-0Relevant academic research and scientific papers
Intermolecular aminocarbonylation of alkenes using concerted cycloadditions of iminoisocyanates
Bongers, Amanda,Clavette, Christian,Gan, Wei,Gorelsky, Serge I.,Betit, Lyanne,Lavergne, Kaitlyn,Markiewicz, Thomas,Moon, Patrick J.,Neves, Nicolas Das,Obhi, Nimrat K.,Toderian, Amy B.,Beauchemin, Andrei M.
, p. 1175 - 1194 (2017/11/14)
The aminocarbonylation of alkenes is a powerful method for accessing the β-amino carbonyl motif that remains underdeveloped. Herein, the development of intermolecular aminocarbonylation reactivity of iminoisocyanates with alkenes is presented. This includes the discovery of a fluorenone-derived reagent, which was effective for many alkene classes and facilitated derivatization. Electron-rich substrates were most reactive, and this indicated that the LUMO of the iminoisocyanate is reacting with the HOMO of the alkene. Computational and experimental results support a concerted asynchronous [3 + 2] cycloaddition involving an iminoisocyanate, which was observed for the first time by FTIR under the reaction conditions. The products of this reaction are complex azomethine imines, which are precursors to valuable β-amino carbonyl compounds such as β-amino amides and esters, pyrazolones, and bicyclic pyrazolidinones. A kinetic resolution of the azomethine imines by enantioselective reduction (s = 13.43) allows access to enantioenriched products. Overall, this work provides a new tool to convert alkenes into β-amino carbonyl compounds.
Kinetic Resolution of Azomethine Imines by Bronsted Acid Catalyzed Enantioselective Reduction
Bongers, Amanda,Moon, Patrick J.,Beauchemin, Andr M.
supporting information, p. 15516 - 15519 (2016/01/26)
Azomethine imines are valuable substrates in asymmetric catalysis, and can be precursors to β-amino carbonyl compounds and complex hydrazines. However, their utility is limited because complex and enantioenriched azomethine imines are often unavailable. R
PROCESS FOR THE SYNTHESIS OF BETA-AMINOCARBONYLS
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Paragraph 00244, (2013/05/23)
The present application provides processes and intermediates useful in the production of β- aminocarbonyl- or β-aminothiocarbonyl-containing compounds. Provided herein is a process for synthesizing β-aminocarbonyl- or β-aminothiocarbonyl-containing compounds from an alkene and a hydrazone. Also provided herein is a process for synthesizing β-aminocarbonyl- or β-aminothiocarbonyl-containing compounds from an alkene and a hydrazine. The present application further provides intermediate aminoisocyanate and iminoisocyanate compounds, and methods for synthesizing the starting hydrazone and hydrazine compounds.
A tunable route for the synthesis of azomethine imines and β-aminocarbonyl compounds from alkenes
Clavette, Christian,Gan, Wei,Bongers, Amanda,Markiewicz, Thomas,Toderian, Amy B.,Gorelsky, Serge I.,Beauchemin, Andre M.
, p. 16111 - 16114,4 (2020/09/09)
Cyclic azomethine imines possessing a β-aminocarbonyl motif are accessed from simple alkene and hydrazone starting materials. A thermal, concerted alkene aminocarbonylation pathway involving an imino-isocyanate intermediate is proposed and supported by DF
