Bis(O-nitrophenyl) Carbonate as a New Reagent for the Synthesis of Chiral Oxazolidin-2-ones

REFERENCES

• Procter , G. Asymmetric Synthesis , Oxford University Press : Oxford , 1999 .
   Google Scholar
• Ager , D. J. ; Prakash , I. ; Schaad , D. R. Chiral oxazolidinones in asymmetric synthesis . Aldrichim. Acta 1997 , 30 , 3 – 11 .
   Web of Science ®Google Scholar
• Kakeya , H. ; Morishita , M. ; Koshino , H. ; Morita , T. I. ; Kobayashi , K. ; Osada , H. Cytoxazone: A novel cytokine modulator containing a 2-oxazolidinone ring produced by Streptomyces sp . J. Org. Chem. 1999 , 64 , 1052 – 1053 .
   PubMed Web of Science ®Google Scholar
• Mishra , R. K. ; Coates , C. M. ; Revell , K. D. ; Turos , E. Synthesis of 2-oxazolidinones from β-lactams: Stereospecific total synthesis of (−)-cytoxazone and all of its stereoisomers . Org. Lett. 2007 , 9 ( 4 ), 575 – 578 .
   PubMedGoogle Scholar
• (a) Zurenko , G. E. ; Ford , C. W. ; Hutchinson , D. K. ; Brickner , S. J. ; Barbachyn , M. R. Oxazolidinone antibacterial agents: Development of the clinical candidates eperezolid and linezolid . Exp. Opin. Invest. Drugs 1997 , 6 , 151 – 158 ; (b) Ntziora , F. ; Falagas , M. E. Linezolid for the treatment of patients with atypical mycobacterial infection: A systematic review . Int. J. Tuberculosis Lung Dis. 2007 , 11 ( 6 ), 606 – 611 ; (c) Burkhardt , O. ; Wilhelm Pletz , M. ; Mertgen , C.-P. ; Welte , T. Linezolid—The first oxazolidinone in the treatment of nosocomial MRSA pneumonia . Rec. Patents Anti-Infect. Drug Discov. 2007 , 2 ( 2 ), 123 – 130 .
   PubMedGoogle Scholar
• Perry , C. M. ; Jarvis , B. Linezolid: A review of its use in the management of serious Gram-positive infections . Drugs 2002 , 61 , 525 – 551 .
   Google Scholar
• Dyen , M. E. ; Swern , D. 2-Oxazolidinones . Chem. Rev. 1967 , 67 , 197 – 237 .
   PubMed Web of Science ®Google Scholar
• Ager , D. J. ; Prakash , I. ; Schaad , D. R. 1,2-Amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis . Chem. Rev. 1996 , 96 , 846 – 849 .
   Google Scholar
• (a) Simon , M. ; Csunderlik , C. ; Tarnaveanu , A. The study of the bis(mononitrophenyl) carbonates synthesis from triphosgene and nitrophenols . Rev. Chim. 2001 , 52 ( 7–8 ), 371 – 376 ; (b) Simon , M. ; Csunderlik , C. ; Jones , P. G. ; Neda , I. ; Tarta-Micle , A. A second polymorph of bis(o-nitrophenyl) carbonate . Acta Cryst. 2003 , E59 , o688 – 690 .
   Google Scholar
• Brunelle , D. J. Novel catalysis of o-nitrophenyl carbonates by p-dimethylaminopyridine . Tetrahedron Lett. 1982 , 23 ( 17 ), 1739 – 1742 .
   Google Scholar
• Simon , M. ; Csunderlik , C. ; Cotarcă , L. ; Căproiu , M. T. ; Neda , I. ; Turoczi , M. C. ; Volpicelli , R. Synthesis of new active o-nitrophenyl carbamates . Synth. Commun. 2005 , 35 ( 11 ), 147 .
   Google Scholar
• Simon , M. ; Micle , A. ; Turoczi , M. C. ; Badea , V. ; Csunderlik , C. Bis(o-nitrophenyl) carbonate, a valid alternative to phosgene in symmetrical N,N′-diaryl ureas synthesis . Rev. Chim. 2006 , 4 , 383 – 386 .
   Google Scholar
• Micle , A. ; Simon , M. ; Csunderlik , C. The study of oxazolidin-2-one synthesis from bis(o-nitrophenyl) carbonate and β-aminoethanol . Rev. Chim. 2006 , 5 ( 57 ), 522 – 524 .
   Google Scholar
• Akiba , T. ; Tamura , O. ; Terashima , S. (4R,5S)-4,5-Diphenyl-3-vinyl-2-oxazolidinone . Org. Synth., Coll. 2004 , 10 , 374 – 375 ; (b) Dismore , C. J. ; Mercer , S. P. Carboxilation and Mitsunobu reaction of amines to give carbamates: Retention vs inversion of configuration is substituent-dependent . Org. Lett. 2004 , 6 ( 17 ), 2885 – 2888 ; (c) Sugiyama , S. ; Morishita , K. ; Chiba , M. ; Ishii , K. Chemoselective debezylation of the N-1-phenylethyl group in 2-oxazolidinones by the anisole–methanesulfonic acid system . Heterocycles 2002 , 57 ( 4 ), 637 ; (d) Chiarotto , I. ; Feroci , M. Palladium-catalyzed electrochemical carbonylation of 2-amino-1-alkanols to oxazolidin-2-ones under very mild conditions . Tetrahedron Lett. 2001 , 42 , 3451 – 3453 ; (e) Knolker , H.-J. ; Braxmeler , T. Synthesis of chiral oxazolidin-2-ones and imidazolin-2-ones via DMAP-catalyzed isocyanation of amines with di-tert-butyl dicarbonate . Tetrahedron Lett. 1998 , 39 , 9407 – 9410 ; (f) Tamura , O. ; Hashimoto , M. ; et al. . Asymmetric synthesis of (1R,2S)-2-fluorocyclopropylamine, the key intermediate of the new generation of quinolonecarboxylic acid, DU-6859 . Tetrahedron Lett. 1992 , 33 ( 24 ), 3487 – 3490 . (g) Newman , M. S. ; Kutner , A. New reactions involving alkaline treatment of 3-nitroso-2-oxazolidones . J. Am. Chem. Soc. 1951 , 4199 – 4204 .
   Google Scholar
• Shen , Y.-M. ; Duan , W.-L. ; Shi , M. Chemical fixation of carbon dioxide co-catalyzed by a combination of Schiff bases or phenols and organic bases . Eur. J. Org. Chem. 2004 , 3080 – 3089 ; (b) Vo , L. ; Ciula , J. ; Gooding , O. W. Chemical development on the chiral auxiliary (S)-4-(phenylmethyl)-2-oxazolidinone utilizing automated synthesis and DoE . Org. Proc. Res. Develop. 2003 , 7 , 514 ; (c) Bartolo , G. ; Mancuso , R. ; Salerno , G. ; Costa , M. An improved procedure for the palladium-catalyzed oxidative carbonylation of β-amino alcohols to oxazolidin-2-ones . J. Org. Chem. 2003 , 68 , 601 – 605 ; (d) Wu , Y. ; Shen , X. A high-yielding low-cost facile synthesis of 2-oxazolidinones chiral auxiliaries . Tetrahedron: Asymmetry 2000 , 11 , 4359 – 4363 ; (e) Gage , J. R. ; Evans , D. A. (S)-4-(Phenylmethyl)-2-oxazolidinone . Org. Synth. Coll. 1993 , 4 , 528 .
   Google Scholar
• (a) Correa , A. ; Denis , J. N. ; Greene , A. E. A safe, simple, one-pot preparation of N-derivatized β-amino alcohols and oxazolidinones from amino acids . Synth. Commun. 1991 , 21 , 1 – 9 ; (b) Wuts , P. G. M. ; Pruitt , L. E. An efficient synthesis of (4S)-(−)-4-isopropyl-2-oxazolidinone . Synthesis 1989 , 622 – 623 ; (c) Kirby , G. W. ; McGuian , H. ; McLean , D. Intramolecular “ene” reactions of transient, allylic, and homoallylic C-nitrosoformate esters . J. Chem. Soc., Perkin Trans. 1 1985 , 1961 – 1966 ; (d) Evans , D. A. ; Mathre , D. J. ; Scott , W. L. Asymmetric synthesis of the enkephalinase inhibitor thiorphan . J. Org. Chem. 1985 , 50 , 1830 – 1835 ; (e) Kleschick , W. A. Selective preparation of isomers and enantiomers of cyclopropane carboxylic acids. US Patent 4479005 A , 1984 .
   Web of Science ®Google Scholar