Ni-catalyzed activation of α-chloroesters: a simple method for the synthesis of α-arylesters and β-hydroxyesters

Tetrahedron

Volumn 63, Issue 5, 2007, Pages 1146-1153

  Durandetti, Muriel ^a   Gosmini, Corinne ^a   Périchon, Jacques ^a  

^a CNRS Université Paris Est Créteil Val de Marne   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; ESTER DERIVATIVE; HALIDE; NICKEL; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROPIONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTRON; PRIORITY JOURNAL; REFORMATSKY REACTION; SYNTHESIS;

EID: 33845603147     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.11.055     Document Type: Article

References (41)

1. For recent reviews of the Reformatsky reaction, see:
2. Ocampo R., and Dolbier Jr. W.R. Tetrahedron 60 (2004) 9325-9374
3. Fürstner A. Synthesis (1989) 571-590
4. Rathke M.W., and Weipert P. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 2 (1991), Elsevier, New York, NY 277-299
5. Fürstner A. In: Knochel P., and Jones P. (Eds). Organozinc Reagents (1999), Oxford University Press, New York, NY 287-305
6. Bentz E., Moloney M.G., and Westaway S.M. Tetrahedron Lett. 45 (2004) 7395-7397
7. Liu X., and Hartwig J.F. J. Am. Chem. Soc. 126 (2004) 5182-5191
8. Hama T., Liu X., Culkin D.A., and Hartwig J.F. J. Am. Chem. Soc. 125 (2003) 11176-11177
9. Orsini F., and Sello G. Curr. Org. Synth. 1 (2004) 111-135
10. Inab S.-I., and Rieke R.D. Tetrahedron Lett. 26 (1985) 155-156
11. Kahiga H., Nishimae S., Shinokubo H., and Oshima K. Tetrahedron 57 (2001) 8807-8815
12. Cahiez G., and Chavant P.-Y. Tetrahedron Lett. 30 (1989) 7373-7376
13. Wessjohann L., and Gabriel T. J. Org. Chem. 62 (1997) 3772-3774
14. Hirashita T., Kinoshita K., Yamamura H., Kawai M., and Araki S. J. Chem. Soc., Perkin Trans. 1 (2000) 825-828
15. Lee P.H., Bang K., Sung S., and Chang S. Synth. Commun. 31 (2001) 3781-3789
16. Connan A., Sibille S., and Périchon J. J. Org. Chem. 56 (1991) 2018-2024
17. Durandetti M., Nédelec J.-Y., and Périchon J. Org. Lett. 3 (2001) 2073-2076
18. Durandetti M., Meignein C., and Périchon J. Org. Lett. 5 (2003) 317-320
19. Durandetti, M.; Périchon, J. Patent application, FR 2004-7230, 2004;
20. Chem. Abstr. 144 (2006) 108097
21. Durandetti M., and Périchon J. Synthesis (2006) 1542-1548
22. Rieu J.P., Boucherle A., Cousse H., and Mouzin G. Tetrahedron 42 (1986) 4095-4131
23. Bakshi S.P., and Turner E.E. J. Chem. Soc. (1961) 171-173
24. Sock O., Troupel M., and Périchon J. Tetrahedron Lett. 26 (1985) 1509-1512
25. Millard A.A., and Rathke M.W. J. Am. Chem. Soc. 99 (1977) 4833-4835
26. Fauvarque J.F., and Jutand A. J. Organomet. Chem. 177 (1979) 273-281
27. Klingstedt T., and Frejd T. Organometallics 2 (1983) 598-600
28. Gooßen L.J. Chem. Commun. (2001) 669-670
29. Durandetti M., Nédélec J.-Y., and Périchon J. J. Org. Chem. 61 (1996) 1748-1755
30. Durandetti M., and Périchon J. Synthesis (2004) 3079-3083
31. Durandetti M., and Périchon J. Tetrahedron Lett. 47 (2006) 6255-6258
32. Fillon H., Gosmini C., and Périchon J. J. Am. Chem. Soc. 125 (2003) 3867-3870
33. Fürstner A., and Shi N. J. Am. Chem. Soc. 118 (1996) 2533-2534
34. Amatore M., Gosmini C., and Périchon J. J. Org. Chem. 71 (2006) 6130-6134
35. Yamamoto Y., and Asao N. Chem. Rev. 93 (1993) 2207-2293
36. Ito A., Kishida M., Kurusu Y., and Masuyama Y. J. Org. Chem. 65 (2000) 494-498
37. de França K.W.R., Navarro M., Léonel E., Durandetti M., and Nédélec J.-Y. J. Org. Chem. 67 (2002) 1838-1842
38. Tamao K., Yamamoto H., Matsumodo H., Miyake N., Hayashi T., and Kumada M. Tetrahedron Lett. 18 (1977) 1389-1392
39. Heiser B., Broger E.A., and Crameri Y. Tetrahedron: Asymmetry 2 (1991) 51-62
40. Uchino M., Asagi K., Yamamoto A., and Ikeda S. J. Organomet. Chem. 84 (1975) 93-103
41. Dunach E., and Périchon J. J. Organomet. Chem. 352 (1988) 239-246