99855-06-8Relevant academic research and scientific papers
The mechanism of the reaction between an aziridine and carbon dioxide with no added catalyst
Phung, Chau,Tantillo, Dean J.,Hein, Jason E.,Pinhas, Allan R.
, (2018)
The mechanism of the reaction at room temperature between an unactivated 2-alkyl aziridine and carbon dioxide to generate the corresponding oxazolidinone in glass has been studied. Theoretical calculations suggest that this reaction should not proceed at room temperature in the absence of a catalyst. In cases where a reaction was observed, kinetic studies show that the reaction displays a zero-order dependence with respect to aziridine, indicating that free aziridine is not involved in the rate-determining step. An ammonium salt generated in situ acts as a catalyst. The amount of this catalyst is diminutive, which prevented spectroscopic identification, and it is not readily removed from the starting material using chromatography.
The high yield and regioselective conversion of an unactivated aziridine to an oxazolidinone using carbon dioxide with ammonium iodide as the catalyst
Phung, Chau,Pinhas, Allan R.
, p. 4552 - 4554 (2010)
The conversion of an unactivated 2-alkylaziridine to the corresponding oxazolidinone generally requires a very high pressure of carbon dioxide, a high temperature, an expensive catalyst, and/or a long reaction time. Here, a new, high yield (over 95%), and highly regioselective (over 95%) conversion of an unactivated aziridine to an oxazolidinone is reported. This reaction is easy to perform because it requires a low pressure of carbon dioxide, low temperature, no co-solvent, and the catalyst is the salt ammonium iodide.
A One-Pot Iodo-Cyclization/Transition Metal-Catalyzed Cross-Coupling Sequence: Synthesis of Substituted Oxazolidin-2-ones from N-Boc-allylamines
Chaumont-Olive, Pauline,Cossy, Janine
supporting information, (2020/05/14)
A one-pot iodo-cyclization/transition metal-catalyzed cross-coupling sequence is reported to access various C5-functionalized oxazolidin-2-ones from unsaturated N-Boc-allylamines. Depending on the Grignard reagents used for the cross-coupling, e.g., aryl- or cyclopropylmagnesium bromide, a cobalt or copper catalyst has to be used to obtain the functionalized oxazolidin-2-ones in good yields.
A Multicomponent Approach to Oxazolidinone Synthesis Catalyzed by Rare-Earth Metal Amides
Zhou, Meixia,Zheng, Xizhou,Wang, Yaorong,Yuan, Dan,Yao, Yingming
, p. 5783 - 5787 (2019/04/14)
Three-component reaction of epoxides, amines, and dimethyl carbonate catalyzed by rare-earth metal amides has been developed to synthesize oxazolidinones. 47 examples of 3,5-disubstituted oxazolidinones were prepared in 13–97 % yields. This is a simple and most practical method which employs easily available substrates and catalysts, and is applicable to a wide range of aromatic and aliphatic amines, as well as mono-substituted epoxides. Scope of disubstituted epoxides is rather limited, which requires further study. Preliminary mechanistic study reveals two possible reaction pathways through intermediates of β-amino alcohols or amides.
The solvent-free and catalyst-free conversion of an aziridine to an oxazolidinone using only carbon dioxide
Phung, Chau,Ulrich, Rani M.,Ibrahim, Mostafa,Tighe, Nathaniel T. G.,Lieberman, Deborah L.,Pinhas, Allan R.
experimental part, p. 3224 - 3229 (2011/12/16)
It has been found for the first time at room temperature that the reaction of an unactivated 2-alkyl or 2-aryl aziridine with carbon dioxide to generate the corresponding oxazolidinone does not need any form of catalysis or solvent to proceed in high yiel
New phenylselanyl group activation: Synthesis of aziridines and oxazolidin-2-ones
Miniejew, Catherine,Outurquin, Francis,Pannecoucke, Xavier
, p. 1575 - 1576 (2007/10/03)
After the study of different phenylselanyl group activators, halogenation by N-bromosuccinimide (NBS) has been shown to be the most suitable manner for cyclizing β-phenylselanyl amines into aziridines and also enabled production of oxazolidin-2-ones from N-Boc β-phenylselanyl amines in excellent yield.
Synthesis of oxazolidinones and 1,2-diamines from N-alkyl aziridines
Hancock, Matthew T.,Pinhas, Allan R.
, p. 2347 - 2355 (2007/10/03)
Reactions of N-alkyl-substituted aziridines with Lil followed by an electrophile are discussed. In the first series of reactions, the electrophile is carbon dioxide and the product is an oxazolidinone. In all cases, either no reaction occurred or a high y
A convenient and inexpensive conversion of an aziridine to an oxazolidinone
Hancock, Matthew T.,Pinhas, Allan R.
, p. 5457 - 5460 (2007/10/03)
The conversion of an aziridine to the corresponding oxazolidinone using only carbon dioxide and a catalytic amount of lithium iodide is discussed. In all cases, either no reaction occurred or a high yield of product was obtained. HMPA has been added to th
N,Se-Acetals: Preparation and Use in Diastereoselective Radical Reactions
Stojanovic, Aleksandar,Renaud, Philippe
, p. 353 - 373 (2007/10/03)
A new facile synthesis of N,S- and N,Se-acetals starting from aldehydes and primary amines is presented (Schemes 3-5). These acetals are used as precursors for stereoselective radical deuteration and allylation reactions (Schemes 6 and 7, Tables 1 and 2). The stereochemical outcome of the reactions depends on the radical trap and the substituents at the N-atom. Deuterations give always anti products with moderate to high selectivities. The allylation reactions give either syn or anti products with low to moderate selectivities. The observed stereoselectivities can be explained with a model based on minimization of A1,3 strain and are controlled by steric and stereoelectronic effects.
