Metal-catalyzed acyl transfer reactions of enol esters: Role of Y5(OiPr)13O and (thd)2Y(OiPr) as transesterification catalysts

Organic Letters

Volumn 2, Issue 7, 2000, Pages 997-1000

  Lin, Mei Huey ^a   RajanBabu, T V ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000736536     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0057131     Document Type: Article

References (31)

1. (a) Procopiou, P. A.; Baugh, S. P. D.; Flack S. S.; Inglis, G. G. A. J. Org. Chem. 1998, 63, 2342 and references therein.
2. (b) Orita, A.; Mitsutome, A.; Otera, J. J. Org. Chem. 1998, 63, 2420.
3. (c) Ishii, Y.; Takeno, M.; Kawasaki, Y.; Muromachi, A.; Nishiyama, Y.; Sakaguchi, S. J. Org. Chem. 1996, 61, 3088.
4. (d) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1996, 61, 4560.
5. (e) Kabouche, Z.; Bruneau, C.; Dixneuf, P. H. Tetrahedron Lett. 1991, 32, 5359.
6. (f) Degueil-Castaing, M.; De Jeso, B.; Drouillard, S.; Maillard, B. Tetrahedron Lett. 1987, 28, 953.
7. (g) See also: Seebach, D.; Hungerbühler, E.; Naef, R.; Schnurrenberger, P.; Weidmann, B.; Züger, M. Synthesis 1982, 138.
8. (a) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813 and references therein.
9. (b) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492 and references cited therin.
10. (c) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169.
11. (d) Yokomatsu, T.; Arakawa, A.; Shibuya, S. J. Org. Chem. 1994, 59, 3506.
12. (e) Evans, D. A.; Anderson, J. C.; Taylor, M. K. Tetrahedron Lett. 1993, 34, 5563.
13. (f) Wang, Y.-F.; Lalonde, J. J.; Momongan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200.
14. 6, and the reaction was followed by GC and NMR. For synthetic applications of Y-alkoxides, see: (a) Anwander. R. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Hermann, W. A., Eds.; VCH: New York, 1996: p 866.
15. (b) Abiko, A.; Wang, G. J. Org. Chem. 1996, 61, 2264.
16. (c) Meguro, M.; Asao, N.: Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 1021.
17. (d) McLain, S. J.; Drysdale, N. E. U.S. Patent 5028667; McLain, S. J.; Drysdale, N. E. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1992, 33, 463.
18. (e) McLain, S. J.; Drysdale, N. E. U.S. Patent 5028667; McLain, S. J.; Drysdale, N. E. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1992, 33, 463.
19. (e) Ford, T. M.; McLain, S. J. U.S. Patent 5208297; Chem. Abstr. 1993, 119, 140012.
20. (f) Ford, T. M.; McLain, S. J. U.S. Patent 5292859; Chem. Abstr. 1994, 121, 58221.
21. (a) Mazdiyasni, K. S.; Lynch, C. T.; Smith, J. S. U.S. Patent 3278571, 1966; Chem. Abstr. 1966, 65, 20008b.
22. (b) Poncelet, O.; Sartain, W. J.; Hubert-Pfalzgraf, L. G.; Folting, K.; Caulton, K. G. Inorg. Chem. 1989, 28, 263.
23. (c) Coan, P. S.; Hubert-Pfalzgraf, L. G.; Caulton, K. G. Inorg. Chem. 1992, 31, 1262.
24. Admittedly, the failed reactions were carried out with 1 M reagents in ethyl acetate with stoichiometric amount of enol ester (ref 1e). In benzene under these conditions 55% conversion was observed.
25. We have no satisfactory explanation for this unusual observation, which is limited to a-amino acid esters. It is likely that the reaction of the amino group with an enol ester is catalyzed by an acid and the Y-alkoxide acts as a scavenger for acidic impurities.
26. 6N).
27. (a) Waller, F. J. Transvinylation catalysts for the production of higher vinylic esters of vinyl acetate. In Catalysis of Organic Reactions; Kosak, J. R., Johnson, T. A., Eds.; Marcel Dekker: New York, 1994; p 397.
28. (b) Ruppin, C.; Dixneuf, P. H. Tetrahedron Lett. 1986, 27, 6323.
29. (c) Murray, R. E. U.S. Patent 5430179, 1995; Chem. Abstr. 1995, 123, 313396.
30. Mitsudo, T.; Hori, Y.; Yamakawa, Y.; Watanabe, Y. J. Org. Chem. 1987, 52, 2230.
31. (e) Rotem, M.; Shvo, Y. Organometallics 1983, 2, 1689.