The silicon-assisted aza-[2,3]-wittig sigmatropic rearrangement

Journal of Organic Chemistry

Volumn 61, Issue 14, 1996, Pages 4820-4823

  Anderson, James C ^a   Siddons, D Craig ^a   Smith, Stephen C ^b   Swarbrick, Martin E ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b JEALOTT S HILL RESEARCH STATION   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000345874     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960329w     Document Type: Article

References (22)

1. Anderson, J. C.; Siddons, D. C.; Smith, S. C.; Swarbrick, M. E. J. Chem. Soc., Chem. Commun. 1995, 1835.
2. Durst, T.; Elzen, R. V. D.; Le Belle, M. J. J. Am. Chem. Soc. 1972, 94, 9261.
3. (a) Ahman, J.; Somfai, P. J. Am. Chem. Soc. 1994, 116, 9781.
4. (b) Coldham, I.; Collis, A. J.; Mould, R. J.; Rathmell, R. E. J. Chem. Soc., Perkin Trans. 1 1995, 2739.
5. (a) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981.
6. (b) Murata, Y.; Nakai, T. Chem. Lett. 1990, 2069.
7. (c) Coldham, I. J. Chem. Soc., Perkin Trans 1 1993, 1275.
8. 4b
9. Gawley, R. E.; Zhang, Q.; Campagna, S. J. Am. Chem. Soc. 1995, 117, 11817.
10. Wu, Y.-D.; Houk, K. N.; Marshall, J. A. J. Org. Chem. 1990, 55, 1421. See also Mikami, K.; Uchida, T.; Hirano, T.; Wu, Y.-D.; Houk, K. N. Tetrahedron 1994 50, 5917.
11. Wu, Y.-D.; Houk, K. N.; Marshall, J. A. J. Org. Chem. 1990, 55, 1421. See also Mikami, K.; Uchida, T.; Hirano, T.; Wu, Y.-D.; Houk, K. N. Tetrahedron 1994 50, 5917.
12. For a recent review see Nakai, T.; Mikami, K. Org. React. 1994, 46, 105.
13. Overman, L. E. J. Am. Chem. Soc. 1976, 98, 2901.
14. These coupling constants may be slightly smaller than one would expect for a trans diaxial coupling, but it is known that electronegative substituents reduce coupling constants. Jackman, L. M.; Sternhell, S. Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry; Pergamon: New York, 1969, p 238 and references therein.
15. Schleyer, P. v R.; Clark, T.; Kos, A. J.; Spitznagel, G. W.; Rohde, C.; Arad, D.; Houk, K. N.; Rondan, N. G. J. Am. Chem. Soc. 1984, 106, 6467.
16. We have also investigated substitution by phenyl and thiophenyl, both of which promote the rearrangement, the results of which will be reported in due course.
17. Trialkylsilyl groups have been used specifically to alter the stereochemica! outcome of the resultant alkenes in oxy-[2,3]-Wittig rearrangements, but we have found no references to their use in control of diastereoselectivity in such rearrangements. Crawley, J. E.; Kaye, A. D.; Pattenden, G.; Roberts, S. M. J. Chem. Soc., Perkin Trans 1 1993, 2001.
18. Chan, T. H.; Mychajlowskij, W.; Ong, B. S.; Harpp, D. N. J. Org. Chem. 1878, 43, 1526.
19. Fleming, I.; Dunoduès, J.; Smithers, R. Org. React. 1989, 37, 57. Protodesilylation of a terminal vinylsilane where the silyl group is on C2 is known to be difficult, presumably because the accepted mechanism would require the formation of an incipient primary carbocation.
20. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
21. Perrin, D. D., Armarego, W. L. F., Eds. Purification of Laboratory Chemicals; Pergamon Press: New York.
22. Prepared according to the procedure outlined in ref 9.