Palladium(II)-catalyzed carbocyclization: Vinylpalladium in 1,4-oxidation of conjugated dienes

Tetrahedron

Volumn 52, Issue 21, 1996, Pages 7511-7523

  Nilsson, Ylva I M ^a   Gatti, Roberto G P ^a   Andersson, Pher G ^a   Bäckvall, Jan E ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE;

CATALYSIS; CONFERENCE PAPER; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 0030010231     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00265-7     Document Type: Conference Paper

References (29)

1. a) Bäckvall, J. E. Pure Appl. Chem. 1992, 64, 429.
2. b) Bäckvall, J. E. in Organometallic Reagents in Organic Synthesis Bateson, J. H.; Mitchell, M. B. Eds.; Academic Press, 1994; pp 81-97.
3. c) Bäckvall, J. E.; Granberg, K. L.; Andersson, P. G.; Gatti, R.; Gogoll, A. J. Org. Chem. 1993, 58, 5445.
4. d) Bäckvall, J. E.; Andersson, P. G. J. Am. Chem. Soc. 1990, 112, 3683.
5. e) Bäckvall, J. E.; Andersson, P. G.; Stone, G. B.; Gogoll, A. J. Org. Chem. 1991, 56, 2988.
6. f) Bäckvall, J. E.; Andersson, P. G. J. Am. Chem. Soc. 1992, 114, 6374.
7. Pd(II)-promoted carbon-carbon bond formation with stabilized carbanions under non-oxidative conditions are known: Hegedus, L. S. in Comprehensive Organic Synthesis, Trost, B. M. and Flemming, I., Eds.; Pergamon: Oxford, U.K., 1992; Vol. 4, pp 571-567.
8. Allyl silanes have recently been used succesfully in these reactions in the presence of catalytic amounts of a Pd(II)-salt. Castaño, A. M.; Bäckvall, J. E. J. Am. Chem. Soc. 1995, 117, 560.
9. a) Kaneda, K.; Uchiyama, T.; Fujiwara, Y.; Imanaka, T.; Teranishi, S. J. Org. Chem. 1979, 44, 55.
10. b) Ma, S.; Lu, X. J. Org. Chem. 1993, 58, 1245.
11. For a preliminary communication, see: Bäckvall, J. E.; Nilsson, Y. I. M.; Andersson, P. G.; Gatti, R. G. P.; Wu, J. Tetrahedron Lett. 1994, 35, 5713.
12. Bäckvall, J. E.; Vågberg, J. O.; Andersson, P. G. Tetrahedron Lett. 1989, 30, 137.
13. Brandsma, L. Preperative Acetylenic Chemistry; Elsevier: Amsterdam, 1988.
14. Bäckvall, J. E.; Gatti, R.; Schink, H. E. Synthesis 1993, 343.
15. The use of methoxyamides in the reaction with Grignard or organolithium reagents to provide ketones has been described by Weinreb: Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815, see also Cupps, T. L.; Boutin, R.H.; Rapoport, H. J. Org. Chem. 1985, 50, 3972.
16. The use of methoxyamides in the reaction with Grignard or organolithium reagents to provide ketones has been described by Weinreb: Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815, see also Cupps, T. L.; Boutin, R.H.; Rapoport, H. J. Org. Chem. 1985, 50, 3972.
17. The identification of the two isomeric π-allyls (described as Z-20' and E-20' in the experimental section) was done by NOE measurements, and NOE-effect was observed on the protons indicated in Figure 2.
18. See for example: Collman, J. P.; Hegedus, L. S.; Norton, L. S.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987; p 416.
19. Bäckvall, J. E.; Nyström, J. E.; Nordberg, R. E. J. Am. Chem. Soc. 1985, 107, 3676-3786.
20. Only substrate 4 gave some 1,4-syn isomer. However, this is due to isomerization of the anti isomer in the presence of LiCl under the reaction conditions. For similar effect, see ref. 3.
21. For the reaction of (π-allyl)palladium intermediates with acetylenes leading to carbocyclization see: Oppolzer, W.; Robyr, C. Tetrahedron 1994, 50, 415.
22. Kosugi, M.; Sakaya, T.; Ogawa, S.; Migita, T. Bull. Chem. Soc. Jpn. 1993, 66, 3058.
23. Zhu, G.; Ma, S.; Lu, X.; J. Chem. Soc. Chem. Commun. 1995, 271.
24. Bäckvall, J. E.; Nilsson, Y. I. M.; Gatti, R. G. P. Organometallics 1995, 14, 4242.
25. For related Pd(0)-catalyzed 1,4-functionalizations of 1,3-dienes with net anti addition see: Takacs, J. M.; Chandramouli, S. V. J. Org. Chem. 1993, 58, 7315.
26. Kharasch, M. S.; Seyler, R. C.; Mayo, F. R. J. Am. Chem. Soc. 1938, 60, 882.
27. Newman, M. S.; Wotiz, J. H. J. Am. Chem. Soc. 1949, 71, 1292.
28. Jolly, R. S.; Luedtke, G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965.
29. Birtwistle, D. H.; Brown, J. M.; Foxton, M. W. Tetrahedron 1988, 44, 7309.