A convenient and inexpensive conversion of an aziridine to an oxazolidinone

Hancock, Matthew T.; Pinhas, Allan R.

doi:10.1016/s0040-4039(03)01325-x

Cited by 86 publications

(58 citation statements)

References 26 publications

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“…; [15][16][17][18][19][20][21] (ii) reaction of propargylamines or propargylic alcohols with CO 2 ; [22][23][24][25][26] (iii) carboxylation of aziridines with CO 2 . [27][28][29][30][31][32][33][34][35][36][37][38][39] Recently, Li et al demonstrated that the oxazolidinones can be synthesized through the copper-catalyzed coupling of aldehydes, amines, terminal alkynes, and CO 2 . [40] Method (iii) is a high-atom-efficiency reaction, utilizing renewable, abundant, and nontoxic CO 2 as a building block, and it has attracted much attention from the viewpoint of green chemistry.…”

Section: Introductionmentioning

confidence: 99%

Proline-Catalyzed Synthesis of 5-Aryl-2-oxazolidinones from Carbon Dioxide and Aziridines Under Solvent-Free Conditions

Dou

Yang

2011

Synthetic Communications

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Natural a-amino acids were proven to be ecofriendly and recyclable catalysts for the carboxylation of aziridines with CO 2 without utilization of any organic solvents or additives. Notably, a series of 5-aryl-2-oxazolidinones were obtained in good yield together with excellent chemo-and regioselectivity under mild conditions using proline as the catalyst. Notably, the catalyst could be recycled more than five times after a simple separation procedure without appreciable loss of catalytic activity. This process represents a promising strategy for homogeneous catalyst recycling.

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Section: Introductionmentioning

confidence: 99%

Proline-Catalyzed Synthesis of 5-Aryl-2-oxazolidinones from Carbon Dioxide and Aziridines Under Solvent-Free Conditions

Dou

Yang

2011

Synthetic Communications

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“…Whereas ambient conditions ( pCO 2 ¼ 1 bar and room temperature) were used for the coupling of 2-methylaziridine with CO 2 , an increase in the reaction temperature (up to 100 C) was required for the conversion of 2-phenylaziridine probably as a result of an increasing steric effect at the ring-opening stage of the reaction. Simultaneously, Pinhas and coworkers reported on the use of an identical metal halide catalyst for the conversion of N-substituted aziridines under similar conditions as those reported by Endo (i.e., ambient conditions) [105]. A dramatic effect of the aziridine substitution on the regio-isomer distribution was observed.…”

Section: Insertion Of Co 2 Into An Aziridine Moietymentioning

confidence: 58%

“…Pinhas [105] studied the formation and stereochemistry of oxazolidinones starting with 2,3-disubstituted aziridines. Using LiI as catalyst, high yields (85-90%) were obtained for dialkyl-substituted aziridines with retention of the starting cis/trans stereochemistry.…”

Section: Insertion Of Co 2 Into An Aziridine Moietymentioning

confidence: 99%

Metal Complexes Catalyzed Cyclization with CO2

Rintjema

Carrodeguas

Laserna

et al. 2015

Topics in Organometallic Chemistry

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This chapter describes in general terms the catalytic methodology that has been made available for the use of carbon dioxide (CO 2 ) in cyclization reactions that incorporate an intact CO 2 fragment without changing the formal oxidation state of the carbon center. The major focus of this chapter will be on the most successful organometallic/inorganic complexes that have been used as catalyst systems throughout the last decade and the preferred ligand frameworks leading to elevated reactivity and/or selectivity behavior in CO 2 coupling reactions. Attention will be especially given to homogeneous catalyst systems as they have proven to be more versatile in CO 2 conversion catalysis and often have modular characteristics that allow for optimization of structure-activity relationships. The most important reactions that have been studied in the current context are designated CO 2 "addition" reactions to small molecule heterocycles such as epoxides and aziridines, though more recently other coupling partners such as diamines, dialcohols, and amino nitriles have further advanced the use of CO 2 in organic synthesis providing access to a wider range of structures. This chapter will serve to demonstrate the utility of CO 2 as a carbon reagent in the catalytic formation of the most prominent organic structures using cyclization strategies specifically.

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“…In this respect, a large number of reports have been published on this kind of CO 2 conversion, such as dual-component system viz. SalenCr(III)/DMAP [14] or Phenol/ DMAP [15], iodine [16,17], alkali metal halide [18][19][20], tetraalkyl ammonium halide [20], and recent naturally occurring amino acids [21]. Particularly, we have reported that PEG functionalized quaternary ammonium bromide [22] and zirconyl chloride [23] were extremely active for this reaction under supercritical CO 2 conditions.…”

Section: Introductionmentioning

confidence: 94%