Relative reactivity of anti- and syn-oximino carbonates and carbamates of 2-pyridylacetic acid esters

Organic Letters

Volumn 3, Issue 14, 2001, Pages 2137-2140

  Kim, Ha Young ^a   Lantrip, Douglas A ^a   Fuchs, Philip L ^a  

^a PURDUE UNIVERSITY   (United States)

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[No Author keywords available]

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ARTICLE;

EID: 0008951088     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015737n     Document Type: Article

References (17)

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2. (b) Luo, J.; Smith, M. D.; Lantrip, D. A.; Wang, S.; Fuchs, P. L. J. Am. Chem. Soc. 1997, 119, 10004.
3. Lee, J. W.; Fuchs, P. L. Org. Lett. 1999, 1, 179.
4. (a) Tannock, I. F.; Rotin, D. Cancer Res. 1989, 49, 4373-4384.
5. (b) Jain, R. K. J. Controlled Release 1998, 53, 49-67.
6. CRC Handbook of Chemistry and Physics values for pyridine-2-carboxaldehyde and the corresponding aldoxime.
7. Jose, B.; Sulatha, M. S.; Pillai, P. M.; Prathapan, S. Synth. Commun. 2000, 30, 1509.
8. Kolar, P.; Petric, A.; Tisler, M. J. Heterocycl. Chem. 1991, 28, 1715.
9. Mathur, N. C.; Goyal, R. N.; Malik, W. U. Indian J. Chem., Sect. A.: Inorg., Bio-inorg., Phys., Theor. Anal. Chem. 1990, 29, 765.
10. Calderwood, D. J.; Davies, R. V.; Rafferty, P.; Twigger, H. L.; Whelan, H. M. Tetrahedron Lett. 1997, 38, 1241.
11. Kolar, P.; Petric, A.; Tisler, M. J. Heterocycl. Chem. 1993, 30, 1253.
12. (a) Thieriet, N.; Alsina, J.; Giralt, E.; Guibe, F.; Albericio, F. Tetrahedron Lett. 1997, 38, 7275-7278.
13. (b) Dessolin, M.; Guillerez, M.-G.; Thieriet, N.; Guibe, F.; Loffet, A. Tetrahedron Lett. 1995, 36, 5741-5744.
14. The oxime esters 12s and 12a were prepared from 5 in parallel fashion to the synthesis of the allyl series (see Supporting Information).
15. X-ray data from these two compounds have been forwarded to the Carbridge Crystalographic Database.
16. Fragmentation of oxime derivatives to benzonitriles has been recently reported: Coskun, N.; Arikan, N. Tetrahedron 1999, 55, 11943.
17. mm x 4.6 mm Econosphere C18, 50/50 acetonitrile/water, 1.0 mL/ min.