[1,2]- and [1,4]-Wittig rearrangements of α-alkoxysilanes: Effect of substitutions at both the migrating benzylic carbon and the terminal sp2 carbon of the allyl moiety

Tetrahedron

Volumn 69, Issue 2, 2013, Pages 849-860

  Onyeozili, Edith N ^a   Mori Quiroz, Luis M ^b   Maleczka Jr , Robert E ^b  

^a FLORIDA A AND M UNIVERSITY   (United States)

^b MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

1,2 Shift; 1,4 Shift; Acylsilanes; Alkoxysilanes; Wittig rearrangement

Indexed keywords

CARBON;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERIZATION; PRIORITY JOURNAL; SUBSTITUTION REACTION; WITTIG REARRANGEMENT;

EID: 84878833643     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.10.091     Document Type: Article

References (24)

1. Tomooka, K.; Yamamoto, H.; Nakai, T. Liebigs Ann. 1997, 1275-1281 and references therein.
2. (a)Marshall, J. A. In ComprehensiveOrganic Synthesis; Pattenden,G., Ed.; Pergamon: London, 1991; Vol. 3, pp 975-1014;
3. (b) Nakai, T.; Mikami, K. Org. React. 1994, 46, 105-209.
4. Felkin, H.; Tambute, A. Tetrahedron Lett. 1969, 10, 821-822.
5. (a) Tomooka, K.; Yamamoto, H.; Nakai, T. Angew. Chem., Int. Ed. 2000, 39, 4500-4502;
6. (b) Rautenstrauch, V. Helv. Chim. Acta 1972, 55, 594-609.
7. Both concerted and a stepwise mechanisms might be operative. (a) Schöllkopf, U. Angew. Chem., Int. Ed. Engl. 1970, 9, 763-773;
8. (b) Felkin, H.; Frajerman, C. Tetrahedron Lett. 1977, 18, 3485-3488.
9. (a) Onyeozili, E. N.; Maleczka, R. E., Jr. Chem. Commun. 2006, 2466-2468;
10. (b) Onyeozili, E. N.; Maleczka, R. E., Jr. Tetrahedron Lett. 2006, 47, 6565-6568.
11. Maleczka, R. E., Jr.; Geng, F. Org. Lett. 1999, 1, 1115-1118.
12. (a) Hayakawa, K.; Hayashida, A.; Kanematsu, K. J. Chem. Soc., Chem. Commun. 1988, 1108-1110;
13. (b) Schlosser, M.; Strunk, S. Tetrahedron 1989, 45, 2649-2664.
14. All a-alkoxysilanes involved in this study were prepared according to the method described Maleczka, R. E., Jr.; Geng, F. Org. Lett. 1999, 1, 1111-1113.
15. For examples of the latter process see:: (a) Nakazaki, A.; Nakai, T.; Tomooka, K. Angew. Chem., Int. Ed. 2006, 45, 2235-2238;
16. (b) Still, W. C. J. Org. Chem. 1976, 41, 3063-3064;
17. (c) Kuwajima, I. J. Organomet. Chem. 1985, 285, 137-148;
18. (d) Danheiser, R. L.; Fink, D. M.; Okano, K.; Tsai, Y.-M.; Szczepanski, S. W. J. Org. Chem. 1985, 50, 5393-5396;
19. (e) Oppolzer, W.; Snowden, R. L.; Simmons, D. P. Helv. Chim. Acta 1981, 64, 2002-2021.
20. Braden, D. A.; Parrack, E. E.; Tyler, D. R. Coord. Chem. Rev. 2001, 211, 279-294.
21. The relative stereochemistry of this diastereomerwas assigned tentatively as syn- 34 by comparison with the 1H NMR of the syn and anti desilylated analogsWada, R.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 8910-8911 Attempts to protodesilylate the [2,3]-Wittig product syn-34 with TBAF or TFA failed.
22. Relative stereochemistry was assigned by oxidizing diastereomeric 31 (1.9:1) to the corresponding carboxylic acid 38: (a) Darcel, C.; Flachsmann, F.; Knochel, P. Chem. Commun. 1998, 205-206;
23. (b) Boudier, A.; Darcel, C.; Flachsmann, f; Micouin, L.; Oestreich, M.; Knochel, P. Chem.-Eur. J. 2000, 6, 2748-2760.
24. Cossrow, J.; Rychnovsky, S. D. Org. Lett. 2002, 4, 147-150.