Treatment of N-Boc derivatives of β-amino alcohols with N,N- diethylaminosulfur trifluoride leads to chiral oxazolidinones: An unexpected intramolecular cyclization

Synlett

Volumn , Issue 8, 1999, Pages 1280-1282

  Zhao, He ^a   Thurkauf, Andrew ^a  

^a NEUROGEN CORPORATION   (United States)

Author keywords

Amino alcohols; Cyclizations; Oxazolidinones

Indexed keywords

2 OXAZOLIDINONE DERIVATIVE; AMINOALCOHOL; CARBONYL DERIVATIVE; DIETHYLAMINE; HETEROCYCLIC COMPOUND; N TERT BUTOXYCARBONYL DERIVATIVE; N,N DIETHYLAMINOSULFUR TRIFLUORIDE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0032790302     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2817     Document Type: Article

References (16)

1. Ager, D. J.; Prakash, J.; Schaad, D. R. Aldrichimica Acta. 1997, 30, 3.
2. Ager, D. J.; Prakash, J.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
3. Curran, T. P.; Pollastri, M. P.; Abelleira, S. M.; Messier, R. J.; McCollum, T. A.; Rowe, C. G. Tetrahedron Lett. 1994, 35, 5409.
4. Agami, C.; Couty, F.; Hamon, L.; Venier, O. Bull. Soc. Chim. Fr. 1995, 132, 808.
5. Agami, C.; Couty, F.; Hamon, L.; Venier O. Tetrahedron Lett. 1993, 34, 4509.
6. Fauq, A. L.: N,N-Diethylaminosulfur trifluoride. In: Paquette, L. A.; Burke, S. D.; Coates, R. M.; Danheiser, R. L.; Denmark, S. E.; Hart, D. J.; Liebeskind, L. S.; Liotta, D. C.; Pearson, A. J.; Reich, H. J.; Rigby, J. H.; Roush, W. R., editors. Encyclopedia of reagents for organic synthesis. New York: John Wiley & Sons Ltd. 1995, Vol. 3, p 1787.
7. Bertini Gross K. M.; Jun, Y. M.; Beak, P. J. Org. Chem. 1997, 62, 7679.
8. 3) δ 156.31, 140.23, 132.28, 127.69, 125.01, 124.50, 114.90, 70.83, 59.04, 35.40; LC-MS (APCI, m/z) 276 (M+1).
9. Imada, Y.; Mitsue, Y.; Ike, K.; Washizuka, K.; Murahashi, S. Bull. Chem. Soc. Jpn. 1996, 69, 2079.
10. Ishizuka, T.; Kimura, K.; Ishibuchi, S.; Kunieda, T. Chem. Lett. 1992, 991.
11. Fodor, G.; Stefanovsky, J.; Kurtev, B. Monatsh. Chem. 1967, 98, 1027.
12. Middleton, W. J. J. Org. Chem. 1975, 40, 574.
13. Konradi, A. W.; Kemp, S. J.; Pedersen, S. F. J. Am. Chem. Soc. 1994, 116, 1316.
14. 3) δ 163.69, 137.55, 129.10 (2C), 128.38 (2C), 126.40, 72.91, 64.35, 57.42, 42.19.
15. Schultz, J. C.; Houle, F. A.; Beauchamp, J. L. J. Am. Chem. Soc. 1984, 106, 3917.
16. O'Brien, P.; Osborne, S. A.; Parker, D. D. J. Chem. Soc. Perkin Trans. 1 1998, 2519.