Axially chiral N-(o-aryl)-4-hydroxy-2-oxazolidinone derivatives from diastereoselective reduction of N-(o-aryl)-2,4-oxazolidinediones: Thermally interconvertible atropisomers via ring-chain-ring tautomerization

Chirality

Volumn 22, Issue 7, 2010, Pages 641-654

  Demir Ordu, Öznur ^a   Doǧan, Ilknur ^a  

^a BOGAZICI UNIVERSITY   (Turkey)

Author keywords

2,4 oxazolidinediones; Axial chirality; Barrier to enantiomerization; Diastereoselective reduction; Enantiomer separation; Enantioselective HPLC; Ring chain ring tautomerization; Temperature dependent NMR

Indexed keywords

2,4 OXAZOLIDINEDIONE DERIVATIVE; 4 HYDROXY 5,5 DIMETHYL 2 OXAZOLIDINONE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE; THERMODYNAMICS;

EID: 77952781523     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20811     Document Type: Article

References (29)

1. Demir Ö, Dogan I. Conformational preferences in diastereomeric (5S)-methyl-3-(o-aryl)-2,4-oxazolidinediones. Chirality 2003;15:242-250.
2. Demir Ordu Ö, Dogan I. Determination of energy barriers to rotation and absolute conformations of thermally interconvertible 5,5-dimethyl-3-(o-aryl) -2,4-oxazolidinedione enantiomers. Tetrahedron: Asymmetry 2004;15:925-933. (Pubitemid 38352836)
3. Demir Ordu Ö , Yilmaz EM, Doǧan İ. Determination of the absolute stereochemistry and the activation barriers of thermally interconvertible heterocyclic compounds bearing a naphthyl substituent. Tetrahedron: Asymmetry 2005;16:3752-3761.
4. Yilmaz EM, Doǧan İ. Axially chiral N-(o-aryl)-2-thioxo- oxazolidine-4-one and rhodanine derivatives: enantiomeric separation and determination of racemization barriers. Tetrahedron: Asymmetry 2008;19: 2184-2191.
5. Seyden-Penne J. Reductions by the alumino- and borohydrides in organic synthesis. Wiley-VCH; 1997. p 45-51.
6. Brière J-F, Charpentier P, Dupas G, Quèguiner G, Bourguignon J. Regioselective reductions of various 3-aminosuccinimides; Application to the synthesis of two heterocyclic systems. Tetrahedron 1997;53: 2075-2086.
7. Clayden J. Non-biaryl atropisomers: new classes of chiral reagents, auxiliaries, and ligands? Angew Chem Int Ed Eng 1997;36:949-951.
8. McCarthy M, Guiry PJ. Axially chiral bidentate ligands in asymmetric catalysis. Tetrahedron 2001;57:3809-3844. (Pubitemid 32385214)
9. Chen Y, Yekta S, Yudin AK. Modified BINOL ligands in asymmetric catalysis. Chem Rev 2003;103:3155-3211.
10. Sinkkonen J, Ovcharenko V, Zelenin KN, Bezhan IP, Chakchir BA, Al- Assar F, Pihlaja K. Stereoisomerism and ring-chain tautomerism in 1- hydroxy-2,3-dihydro-1H-pyrazo(1,2-a)pyridazine-5,8-diones and 1- hydroxy- and 1-amino-2,3-dihydro-1H-pyrazolo(1,2-b)phthalazine-5,10- diones. Eur J Org Chem 2002;20:3447-3454.
11. Prashad M, Har D, Kim H-Y, Repic O. A new, economical, practical and racemization-free method for the reductive removal of 2-oxazolidinones from N-acyloxazolidinones with sodium borohydride. Tetrahedron Lett 1998;39:7067-7070. (Pubitemid 28414784)
12. Valters RE, Flitsch W. Ring-chain tautomerism. Newyork: Plenum Press; 1985.
13. Valters R. The electronic and steric effects in heterolytic intramolecular cyclisation reactions. Russ Chem Rev 1982;51:788-801.
14. Bowden K, Hiscocks SP, Perjéssy A. Ring-chain tautomerism. Part 9: 1 2-Acylbenzamides, 8-acyl-1-naphthamides and 5-acyl-4-phenanthramides. J Chem Soc Perkin Trans 2 1998;291-295.
15. Sinkkonen J, Zelenin KN, Potapov A-K, Lagoda IV, Alekseyev VV, Pihlaja K. Ring-chain tautomerism in 2-substituted 1,2,3,4-tetrahydroquinazolines A 1H, 13C and 15N NMR study. Tetrahedron 2003;59:1939-1950.
16. Maloshitskaya O, Sinkkonen J, Ovcharenko V, Zelenin KN, Pihlaja K. Chain-ring-chain tautomerism in 2-aryl-substituted hexahydropyrimidines and 1H-2,3-dihydroperimidines. Does it appear? Tetrahedron 2004;60:6913-6921. (Pubitemid 38917226)
17. Coskun N, Asutay O. Imidazolidin-1-oles, N-2-aminoethyl nitrones and 1,2,5-oxadiazinanes. A novel ring-chain tautomerism. Tetrahedron Lett 2007;48:5151-5155.
18. Tóth D, Szatmári I, Fülöp F. Substituent effects in the ring-chain tautomerism of 1-alkyl-3-arylnaphth-[1,2-e][1,3]oxazines. Eur J Org Chem 2006;20:4664-4669.
19. Juhász M, Lázár L, Fülöp F. Substituent effects in the ring-chain tautomerism of 4-alkyl-2-aryl substituted oxazolidines and tetrahydro-1,3-oxazines. J Heterocycl Chem 2007;44:1465-1473. (Pubitemid 351225786)
20. Maloshitskaya O, Sinkkonen J, Alekseyev VV, Zelenin KN, Pihlaja K. A comparison of ring-chain tautomerism in heterocycles derived from 2-aminobenzenesulfonamide and anthranilamide. Tetrahedron 2005; 61:7294-7303. (Pubitemid 40840636)
21. Alberty RA, Silbey RJ, Physical chemistry. Newyork: Wiley; 1992. p 501-502.
22. Roussel C, Adjimi M, Chemlal A, Djafri A. Comparison of racemization processes in 1-arylpyrimidine-2-thione and 3-arylthiazoline-2-thione atropisomers and their oxygen analogues. J Org Chem 1988;53:5076-5080.
23. Pham-Guy C, Villain-Pautet G, Hua H, Chikhi-Chorfi N, Galons H, Thevenin M, Claude J-R, Warnet J-M. Separation of oxazepam, lorazepam, and temazepam enantiomers by HPLC on a derivatized cyclodextrin-bonded phase: application to the determination of oxazepam in plasma. J Biochem Biophys Methods 2002; 54:287-299. (Pubitemid 36126148)
24. Trapp O, Trapp G, Schurig V. Direct calculation and computer simulation of the enantiomerization barrier of oxazepam in dynamic HPLC experiments-a comparative study. J Biochem Biophys Methods 2002; 54:301-313. (Pubitemid 36126149)
25. Lázár L, Göblyös A, Martinek TA, Fülöp F. Ring-Chain tautomerism of 2-aryl-substituted cis- and trans- Decahydroquinazolines. J Org Chem 2002;67:4734-4741. (Pubitemid 34742703)
26. Szatmári I, Martinek TA, Lázár L, Koch A, Kleinpeter E, Neuvonen K, Fülöp F. Stereoelectronic effects in ring-chain tautomerism of 1,3-diarylnaphth[ 1,2-e][1,3]oxazines and 3-alkyl-1-arylnaphth[1, 2-e][1,3]oxazines. J Org Chem 2004;69:3645-3653.
27. Beesley RM, Ingold CK, Thorpe JF. CXIX.-The formation and stability of spiro-compounds. I. Spiro-compounds from cyclohexane. J Chem Soc Trans 1915;107:1080-1106.
28. Dogan I, Burgemeister T, Içli S, Mannschreck A. Synthesis and NMR studies of chiral 4-oxazolidinones and rhodanines. Tetrahedron 1992; 48:7157-7164.
29. Friebolin H. Basic one- and two dimensional NMR spectroscopy. Wiley-VCH; 2005. p 305-310.