Decarboxylative isomerization of N-Acyl-2-oxazolidinones to 2-oxazolines

Journal of Organic Chemistry

Volumn 73, Issue 8, 2008, Pages 3292-3294

  May, Aaron E ^a   Willoughby, Patrick H ^a   Hoye, Thomas R ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ISOMERIZATION; LITHIUM COMPOUNDS; LOW TEMPERATURE EFFECTS; PROTONS;

DECARBOXYLATIVE ISOMERIZATION; LITHIUM IODIDE;

AMINES;

AMINE; IODIDE; LITHIUM DERIVATIVE; METAL; OXAZOLIDINONE DERIVATIVE; OXAZOLINE DERIVATIVE;

ARTICLE; BIOTRANSFORMATION; CATALYST; CYCLIZATION; DECARBOXYLATION; ISOMERIZATION; LOW TEMPERATURE; QUANTUM YIELD; REACTION ANALYSIS; RING OPENING; STEREOCHEMISTRY;

ACYLATION; CARBOXYLIC ACIDS; CYCLIZATION; IODIDES; ISOMERISM; LITHIUM; MOLECULAR STRUCTURE; OXAZOLES;

EID: 42149113561     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800076f     Document Type: Article

References (20)

1. Bertram, A.; Pattenden, G. Nat. Prod. Rep. 2007, 24, 18-30.
2. Pirrung, M. C.; Tumey, L. N.; McClerran, A. L.; Raetz, C. R. H. J. Am. Chem. Soc. 2003, 125, 1575-1586.
3. Desimoni, G.; Faita, G.; Jorgensen, K. A. Chem. Rev. 2006, 106, 3561-3651.
4. Kobayashi, S.; Uyama, H.; Narita, Y.; Ishiyama, J. Macromolecules 1992, 25, 3232-3236.
5. (a) Mundy, B. P.; Kim, Y. J. Heterocycl. Chem. 1982, 19, 1221-1222.
6. (b) Foris, A.; Neumer, J. F. Magn. Reson. Chem. 2005, 43, 867-868.
7. (a) Cook, G. R.; Shanker, S. P. J. Org. Chem. 2001, 66, 6818-6822.
8. (b) Cook, G. R.; Shanker, S. P. Tetrahedron Lett. 1998, 39, 3405.
9. (c) Cook, G. R.; Manivannan, E.; Underdahl, T.; Lukacova, V.; Zhang, Y.; Balaz, S. Bioorg. Med. Chem. Lett. 2004, 19, 4935-4939.
10. Intervention of N-alkylation to generate an N-acylaziridine cannot be excluded since, via the Heine rearrangement, these are known to ring open and isomerize to 2-oxazolines in the presence of iodide ion: (a) Heine, H. W.; Kenyon, W. G.; Johnson, E. M. J. Am. Chem. Soc. 1961, 83, 2570-2574.
11. (b) Kurti, L.; Czako, B. Strategic Applications of Named Reactions in Organic Synthesis; Elsevier Academic Press: London, 2005; pp 198-199.
12. For the synthesis of anti-aldol adducts, see: Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392-393.
13. 1H NMR spectrum of the oxazoline product 8 indicated that it was essentially one diastereomer.
14. For general reviews on oxazoline formation and usage, see: (a) Frump, J. A. Chem. Rev. 1971, 71, 483-505.
15. (b) Reuman, M.; Meyers, A. I. Tetrahedron 1985, 41, 837-860.
16. (c) Kronek, J.; Luston, J.; Boehme, F. Chem. Listy 1998, 92, 175-185.
17. Hedayatullah, M.; Brault, J. F. Phosporus Sulfur 1981, 11, 303-310.
18. Treatment of 10 with DBU led to consumption and generation of baseline TLC material. Although this was not further explored, the presumed intermediate tosylaziridine would be expected to undergo ring opening by the nucleophilic DBU to form an ammonium salt: Moon, B.; Han, S.; Kim, D. Org. Lett. 2005, 7, 3359-3361.
19. We are aware of a single example of aziridine formation from an N-alkyloxazolidinone in which TMSI was used as the reagent. See: Lakanen, J. R.; Pegg, A. E.; Coward, J. K. J. Med. Chem. 1995, 38, 2714-2727.
20. For the synthesis of thioacylated carbamates, see: Wagner, G.; Leistner, S. Pharmazie 1972, 27, 547-552.