- A method for synthesis of acylated oxazolidone
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The invention discloses a method for synthesis of acylated oxazolidone. Synthesis method of the invention, comprising the following steps: in the non-protic organic solvent, the compound III and under the action of an acid, the compound I with compound II carries out amidation reaction, to obtain compound IV. The method of the invention can be conducted under mild conditions, high yield, high purity, and is suitable for industrial production requirements.
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Paragraph 0028; 0029; 0030; 0040; 0041; 0042
(2019/01/08)
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- Novel approach to stereoselective synthesis of (E)/(Z)-(N-acyl-oxazolidinone)-eneglycinates
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(E)-(N-Acyl-oxazolidinone)-eneglycinates were synthesized with high stereoselectivity and in good yield by condensation of aldehydes with glycinates. (Z)-Eneglycinates could be prepared in high purity and moderate yield by transformation of (E)-eneglycinates under mild conditions. The effect on the (E)/(Z)-configuration of eneglycinates of steric hindrance by ?±-substituents on the aldehyde was also examined. The software MMFF94 was used to explain the transformation of the thermodynamic product into the kinetic product and a plausible mechanism is given.
- Zhang, Yanyan,Sun, Haopeng,You, Qidong
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p. 749 - 760
(2015/03/03)
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- Absolute configuration of lactams and oxazolidinones using kinetic resolution catalysts
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A simple method for determining the absolute configuration of oxazolidinones, lactams, and their derivatives using kinetic resolution catalysts is described. The optically pure substrates were acylated using the (S)-HBTM and the (R)-HBTM catalyst, and the faster reaction was determined. An empirical mnemonic was developed for the assignment of the absolute configuration based on the fast-reacting catalyst.
- Perry, Matthew A.,Trinidad, Jonathan V.,Rychnovsky, Scott D.
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supporting information
p. 472 - 475
(2013/04/11)
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- Kinetic resolution of 2-oxazolidinones via catalytic, enantioselective N-acylation
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Kinetic resolution of racemic 2-oxazolidinones via catalytic, enantioselective N-acylation has been achieved for the first time and with outstanding selectivities. Copyright
- Birman, Vladimir B.,Jiang, Hui,Li, Ximin,Guo, Lei,Uffman, Eric W.
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p. 6536 - 6537
(2007/10/03)
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- Development of a scalable process for 1-β-methyl azetidinone: A carbapenem key intermediate
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An optimized process for the stereoselective synthesis of 1-β-methyl carbapenem key intermediate (3S,4S)-[(R)-1′-((tert-butyldimethylsilyl)oxy) ethyl]-4-[(R)-1-carboxyethyl]-2-azetidinone (1) and (3R,4R)-4-acetoxy-3-[(R)- 1′-((tert-butyldimethylsilyl)oxy)ethyl]-2-azetidinone has been developed employing commercially available chiral 4-phenyl-2-oxazolidinone. This method provides an efficient and cost-effective process with improved selectivity and higher yield.
- Tewari, Neera,Nizar, Hashim,Rai, Bishwa Prakash,Mane, Avinash,Prasad, Mohan
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p. 827 - 829
(2012/12/26)
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- Simple and efficient N-acylation reactions of chiral oxazolidinone auxiliaries
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A simplified procedure for the N-acylation of oxazolidin-2-one chiral auxiliaries has been developed. The acylations occur at room temperature in the presence of triethylamine and catalytic quantities of 4-(N,N-dimethylamino)pyridine, thereby eliminating the necessity for a strong base such as butyllithium. Acylations with both symmetrical and mixed anhydrides, as well as acid chlorides, occur with a wide variety of oxazolidinone auxiliaries.
- Ager, David J.,Allen, David R.,Schaad, David R.
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p. 1283 - 1285
(2007/10/03)
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