Efficient preparation of trisubstituted alkenes using the Julia-Lythgoe olefination of ketones. On the key-role of SmI2 in the reductive elimination step

Tetrahedron Letters

Volumn 37, Issue 12, 1996, Pages 2089-2092

  Markó, István E ^a   Murphy, Fiona ^a   Dolan, Simon ^b  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030005954     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00200-6     Document Type: Article

References (15)

1. a. Julia, M.; Paris, J. M. Tetrahedron Lett., 1973, 4833.
2. b. Kocienski, P. in Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I. Eds., 1991, 6, 987.
3. For a pertinent example, see: Barrett, A. G. M.; Carr, R. A. E.; Attwood, S. V.; Richardson, G.; Walshe, N. D. A. J. Org. Chem., 1986, 51, 4840.
4. The mechanism of the Julia olefination reaction has recently been challenged. Keck, G. E.; Savin, K. A.; Welgarz, M. A. J. Org. Chem., 1995, 60, 3194.
5. For excellent reviews, see: a. Kagan, H. B.; Sasaki, M.; Collin, J. Pure Appl. Chem., 1988, 60, 1725.
6. b. Molander, G. A. Chem. Rev., 1992, 92, 29.
7. 2 in THF has been reported: Kuenzer, H.; Stahnke, M.; Sauer, G.; Wiechert, R. Tetrahedron Lett., 1991, 32, 1949.
8. Kende, A. S.; Mendoza, J. S. Tetrahedron Lett., 1990, 31, 7105.
9. These include, inter alia, HMPA, DMPU, Fe(II) and Fe(III) salts.
10. a. Inanaga, J.; Ishikawa, M.; Yamaguchi, M. Chem. Lett., 1987, 1485.
11. b. Ujikawa, O.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett., 1989, 30, 2387.
12. 2-mediated reductive elimination of a β-acetoxysulfone has been reported in the literature: de Pouilly, P.; Chenede, A.; Mallet, J. M.; Sinaÿ, P. Bull. Soc. Chim. Fr. 1993, 130, 256. We thank Professor Sinay for bringing this reference to our attention.
13. Fukumoto, K.; Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y. Synlett., 1994, 895.
14. The reduction of the benzoate function of Taxol into the corresponding alkane using electrochemistry has been shown to occur chemoselectively at -78°C (Dr Alain Commerçon, personal communication, Deauville, 1995). We are extremely grateful to Dr Commerçon for communicating us this unpublished observation.
15. Recently, Mg has been used to effect the Julia-Lythgoe reduction elimination: Lee, G. H.; Lee, H. K.; Choi, E. B.; Kin, B. T.; Pak, C. S. Tetrahedron Lett., 1995, 36, 5607.