Synthesis and chemistry of bridgehead allylsilanes. Stereoselective reactions with aldehydes

Organic Letters

Volumn 7, Issue 18, 2005, Pages 3913-3916

  Lauchli, Ryan ^a   Whitney, John M ^a   Zhu, Liang ^a   Shea, Kenneth J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; CATALYSIS; MOLECULAR STRUCTURE; SILANES; STEREOISOMERISM;

EID: 24944486016     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051363c     Document Type: Article

References (22)

1. (a) Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375.
2. (b) Majetich, G. Org. Synth.: Theor. Appl. 1989, 1, 173.
3. (c) Hosomi, A. Acc. Chem. Res. 1988, 21, 200.
4. (a) Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063.
5. (b) Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763.
6. (c) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293.
7. Some recent examples include: (a) Mulzer, J.; Hanbauer, M. Tetrahedron Lett. 2002, 43, 3381.
8. (b) Su, Q. B.; Panek, J. S. J. Am. Chem. Soc. 2004, 126, 2425.
9. (c) Su, Q. B.; Panek, J. S. Angew. Chem., Int. Ed. 2005, 44, 1223.
10. Whitney, J. M.; Parnes, J. S.; Shea, K. J. J. Org. Chem. 1997, 62, 8962.
11. Bear, B. R.; Sparks, S. M.; Shea, K. J. Angew. Chem., Int. Ed. 2001, 40, 820.
12. (a) Cahiez, G.; Alexakis, A.; Normant, J. F. Tetrahedron Lett. 1978, 19, 3013.
13. (b) Umio, S.; Ueda, I.; Nojima, H. J. Med. Chem. 1972, 15, 855.
14. (a) Hosomi, A.; Saito, M.; Sakurai, H. Tetrahedron Lett. 1979, 20, 429.
15. (b) Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1985, 26, 5175.
16. Lewis acid promoted reactions were also attempted but were unsuccessful, although intermolecular reactions of similar untethered dienes proceed readily. (a) Organ, M. G.; Winkle, D. D. J. Org. Chem. 1997, 62, 1881.
17. (b) Organ, M. G.; Winkle, D. D.; Huffmann, J. J. Org. Chem. 1997, 62, 5254.
18. (a) Warner, P. M. Chem. Rev. 1989, 89, 1067.
19. (b) Lease, T. J.; Shea, K. J. Adv. Theor. Interest. Mol. 1992, 2, 79.
20. Lambert, J. B.; Zhao, Y.; Emblidge, R. W.; Salvador, L. A.; Liu, X.; So, J.-H.; Chelius, E. C. Acc. Chem. Res. 1999, 32, 183.
21. 2,6-Di-tert-butyl-4-methylpyridine was used as the proton scavenger.
22. Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66.