160424-29-3Relevant articles and documents
Carbon dioxide as a carbonylating agent in the synthesis of 2-oxazolidinones, 2-oxazinones, and cyclic ureas: Scope and limitations
Paz, Jairo,Perez-Balado, Carlos,Iglesias, Beatriz,Munoz, Luis
experimental part, p. 3037 - 3046 (2010/07/15)
Carbon dioxide can be used as a convenient carbonylating agent in the synthesis of 2-oxazolidinones, 2-oxazinones, and cyclic ureas. The transient carbamate anion generated by treating a primary or secondary amine group in basic media can be activated with phosphorylating agents such as Diphenylphosphoryl azide (DPPA) and Diphenyl chlorophosphate (DPPCl) but also with other types of electrophiles such as SOCl2, TsCl, or AcCl. The intramolecular trapping of the activated carbamate by a hydroxyl group leads to the formation of 2-oxazolidinones or 2-oxazinones in good to excellent yields. This methodology was successfully applied to the synthesis of cyclic ureas up to 7-membered rings from the corresponding diamines.
Organocatalytic enantioselective synthesis of nitrogen-substituted dihydropyran-2-ones, a key synthetic intermediate of 1β-methylcarbapenems
Kobayashi, Shoji,Kinoshita, Tatsuhiro,Uehara, Hisatoshi,Sudo, Tomoko,Ryu, Llhyong
supporting information; experimental part, p. 3934 - 3937 (2009/12/05)
Organocatalytic enantioselective cycloadditions providing nitrogen-substituted dihydropyran-2-ones were developed in two catalytic systems. The (3R,4R)-product was a versatile intermediate in the synthesis of 1β-methylcarbapenem antibiotics.
Carbonylation with CO2 and phosphorus electrophiles: A convenient method for the synthesis of 2-oxazolidinones from 1,2-amino alcohols
Paz, Jairo,Pérez-Balado, Carlos,Iglesias, Beatriz,Mu?oz, Luis
scheme or table, p. 395 - 398 (2009/08/09)
2-Oxazolidinones were prepared in good yields from 1,2-amino alcohols and CO2 in the presence of tetramethyl-phenylguanidine (PhTMG) as a base and a variety of phosphorus electrophiles under mild conditions. This procedure is advantageous over previous methodologies and relies on a novel carbonylation procedure that utilizes nontoxic CO2 and phosphorus electrophiles. Georg Thieme Verlag Stuttgart.
Highly efficient asymmetric Michael addition of aldehydes to nitroalkenes catalyzed by a simple trans-4-hydroxyprolylamide
Palomo, Claudio,Vera, Silvia,Mielgo, Antonia,Gomez-Bengoa, Enrique
, p. 5984 - 5987 (2007/10/03)
Discriminating reactions: While no self-aldol reaction is observed in the reaction shown, catalyst 1 promotes the Michael addition of aldehydes to nitroalkenes with the lowest catalyst loading and lowest stoichiometric ratio of reactant aldehyde that have
Fluorinated chiral secondary amines as catalysts for epoxidation of olefins with oxone
Ho, Chun-Yu,Chen, Ying-Chun,Wong, Man-Kin,Yang, Dan
, p. 898 - 906 (2007/10/03)
(Chemical Equation Presented) We have synthesized a series of chiral cyclic secondary amines having different substitution patterns and have screened them as catalysts for the asymmetric epoxidation of olefins using Oxone. The highest enantiomeric excess (61%) occurred for the epoxidation of 1-phenylcyclohexene catalyzed by a secondary amine bearing a fluorine atom at the β-position relative to the amino center. Our experimental results provide further support to the notion that the amine plays a dual role - as a phase transfer catalyst and an Oxone activator - in these epoxidation reactions. The slightly acidic reaction conditions we employed in this work obviate the need to preform ammonium salts, which are the actual catalysts that mediate the epoxidations.
Oxazaborolidines as functional monomers: Ketone reduction using polymer-supported Corey, Bakshi, and Shibata catalysts
Price, Michael D.,Sui, Jennifer K.,Kurth, Mark J.,Schore, Neil E.
, p. 8086 - 8089 (2007/10/03)
The first two polymer-supported versions of the Corey, Bakshi, and Shibata (CBS) catalyst have been prepared. Functional monomers based structurally upon the original B-methylated catalyst have been used to prepare catalytic polymers containing the CBS moiety bound both in a pendant fashion and in the form of a cross-link. Enantioselective reductions of two prochiral ketones have been carried out using the original catalyst in the solution phase as well as the two solid-state systems. While the pendant-bound system shows reduced stereoselectivity, the cross-linked version affords enantioselectivities almost identical to those of the solution-phase model.
A short synthesis of (S)-2-(diphenylmethyl) pyrrolidine, a chiral solvating agent for NMR analysis
Bailey, David J.,O'Hagan, David,Tavasli, Mustafa
, p. 149 - 153 (2007/10/03)
A three step synthesis of (S)-2(diphenylmethyl)pyrrolidine 4 is described which allows its preparation on a large scale. The C2 symmetric diamines 5 and 6 have been prepared from 4 and are attractive as potential ligands for asymmetric transformations. Pyrrolidine 4 has been assessed as a chiral solvating agent for the NMR analysis of chiral compounds. It emerges as a good CSA for carboxylic acids and some secondary alcohols.
A New Route to Oxazolidinones
Delaunay, Dominique,Corre, Maurice Le
, p. 3041 - 3042 (2007/10/02)
The oxazolidinones 5 and 7 have been prepared by coupling Grignard reagents with N-alkoxycarbonyl-α-amino esters.Hydrolysis of oxazolidinones 5 afforded β-amino alcohols with good yield and enantiomeric excess.
