Improved ester interchange catalysts

Organic Letters

Volumn 2, Issue 26, 2000, Pages 4209-4212

  Kissling, Rebecca M ^a   Gagné, Michel R ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000815202     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0067585     Document Type: Article

References (22)

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3. (b) Jackman, L. M.; Smith, B. D. J. Am. Chem. Soc. 1988, 110, 3829-3835, and references therein.
4. (c) Schmidt, P.; Lochmann, L.; Scneider, B. J. Mol. Struct. 1971, 9, 403-411.
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7. (f) Chisholm, M. H.; Drake, S. R.; Naiini, A. A.; Streib, W. E. Polyhedron 1991, 10, 805-810.
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10. Pregel, M. J.; Dunn, E. J.; Nagelkerke, R.; Thatcher, G. R. J.; Buncel, E. Chem. Soc. Rev. 1995, 449-455.
11. Stanton, M. G.; Allen, C. B.; Kissling, R. M.; Lincoln, A. L.; Gagné, M. R. J. Am. Chem. Soc. 1998, 120, 5981-5989.
12. For a related transesterification protocol that equilibrates alcohols and esters using KOMe/18-c-6, see: Rowan, S. J.; Hamilton, D. G.; Brady, P. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1997, 119, 2578-2579.
13. Stanton, M. G.; Gagné, M. R. J. Org. Chem. 1997, 62, 8240-8242.
14. Kissling, R. M.; Gagné, M. R. J. Org. Chem. 1999, 64, 1585-1590.
15. Weiss, E. Z. Anorg. Allg. Chem. 1964, 332, 197-203.
16. For relevant examples of characterized mixed alkali metal alkoxide, aryloxide, or acetylide clusters, see: (a) Jackman, L. M.; Rakiewicz, E. F. J. Am. Chem. Soc. 1991, 113, 1202-1210.
17. (b) Jackman, L. M.; Rakiewicz, E. F.; Benesi, A. J. J. Am. Chem. Soc. 1991, 113, 4101-4109.
18. (c) Thompson, A.; Corley, E. G.; Huntington, M.; Grabowski, E. J. J.; Remenar, J. F.; Collum, D. B. J. Am. Chem. Soc. 1998, 120, 2028-2038.
19. iPrOAc dimethyl methylphosphonate (DMMP) 11%, isopropyl methyl methylphosphonate (IMMP) 51%; diisopropyl methylphosphonate (DIMP) 38%.
20. Control experiments showed that NaOAr is not a competent catalyst.
21. NMR experiments indicate that at this ratio some 2:2 and 0:4 also exist in solution, the former of which undoubtedly contributes to catalysis as well.
22. 4.