Scope and Limitations in Palladium-Catalyzed Substitution Reactions of Unsaturated Fused Lactones

Journal of Organic Chemistry

Volumn 62, Issue 14, 1997, Pages 4665-4671

  Aggarwal, Varinder K ^a   Monteiro, Nuno ^a   Tarver, Gary J ^a   McCague, Ray ^b  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b Chiroscience Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000066341     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962106b     Document Type: Article

References (47)

1. For recent reviews on π-allyl palladium complexes see: Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257-276. Godlesky, S. A. In Comprehensive Organic Synthesis; Troat, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 4, p 585. Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089-1122.
2. For recent reviews on π-allyl palladium complexes see: Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257-276. Godlesky, S. A. In Comprehensive Organic Synthesis; Troat, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 4, p 585. Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089-1122.
3. For recent reviews on π-allyl palladium complexes see: Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257-276. Godlesky, S. A. In Comprehensive Organic Synthesis; Troat, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 4, p 585. Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089-1122.
4. Heumann, A.; Réglier, M. Tetrahedron 1995, 51, 975-1015.
5. Nucleophilic substitution of allylic acetates has also proved to be a particularly efficient method for the preparation of 1,4-cis-disubstituted cyclopent-2-enes. For general studies on palladium-mediated alkylation of cyclopentenyl acetates and related compounds see: Valpey, R. S.; Miller, D. J.; Estes, J. M.; Godleski, S. J. Org. Chem. 1982, 47, 4717-4720. Deardorff, D. R.; Linde, R. G., II; Martin, A. M.; Shulman, M. J. J. Org. Chem. 1989, 54, 2759-2762 and references cited therein. Gundersen, L. L.; Benneche, T.; Rise, F.; Gogoll, A.; Undheim, K. Acta Chem. Scand. 1992, 46, 761-771. Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327-9343. Shibasaki, M.; Nukui, S.; Mori, M. Chem. Lett. 1991, 1791-1800.
6. Nucleophilic substitution of allylic acetates has also proved to be a particularly efficient method for the preparation of 1,4-cis-disubstituted cyclopent-2-enes. For general studies on palladium-mediated alkylation of cyclopentenyl acetates and related compounds see: Valpey, R. S.; Miller, D. J.; Estes, J. M.; Godleski, S. J. Org. Chem. 1982, 47, 4717-4720. Deardorff, D. R.; Linde, R. G., II; Martin, A. M.; Shulman, M. J. J. Org. Chem. 1989, 54, 2759-2762 and references cited therein. Gundersen, L. L.; Benneche, T.; Rise, F.; Gogoll, A.; Undheim, K. Acta Chem. Scand. 1992, 46, 761-771. Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327-9343. Shibasaki, M.; Nukui, S.; Mori, M. Chem. Lett. 1991, 1791-1800.
7. Nucleophilic substitution of allylic acetates has also proved to be a particularly efficient method for the preparation of 1,4-cis-disubstituted cyclopent-2-enes. For general studies on palladium-mediated alkylation of cyclopentenyl acetates and related compounds see: Valpey, R. S.; Miller, D. J.; Estes, J. M.; Godleski, S. J. Org. Chem. 1982, 47, 4717-4720. Deardorff, D. R.; Linde, R. G., II; Martin, A. M.; Shulman, M. J. J. Org. Chem. 1989, 54, 2759-2762 and references cited therein. Gundersen, L. L.; Benneche, T.; Rise, F.; Gogoll, A.; Undheim, K. Acta Chem. Scand. 1992, 46, 761-771. Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327-9343. Shibasaki, M.; Nukui, S.; Mori, M. Chem. Lett. 1991, 1791-1800.
8. Nucleophilic substitution of allylic acetates has also proved to be a particularly efficient method for the preparation of 1,4-cis-disubstituted cyclopent-2-enes. For general studies on palladium-mediated alkylation of cyclopentenyl acetates and related compounds see: Valpey, R. S.; Miller, D. J.; Estes, J. M.; Godleski, S. J. Org. Chem. 1982, 47, 4717-4720. Deardorff, D. R.; Linde, R. G., II; Martin, A. M.; Shulman, M. J. J. Org. Chem. 1989, 54, 2759-2762 and references cited therein. Gundersen, L. L.; Benneche, T.; Rise, F.; Gogoll, A.; Undheim, K. Acta Chem. Scand. 1992, 46, 761-771. Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327-9343. Shibasaki, M.; Nukui, S.; Mori, M. Chem. Lett. 1991, 1791-1800.
9. Nucleophilic substitution of allylic acetates has also proved to be a particularly efficient method for the preparation of 1,4-cis-disubstituted cyclopent-2-enes. For general studies on palladium-mediated alkylation of cyclopentenyl acetates and related compounds see: Valpey, R. S.; Miller, D. J.; Estes, J. M.; Godleski, S. J. Org. Chem. 1982, 47, 4717-4720. Deardorff, D. R.; Linde, R. G., II; Martin, A. M.; Shulman, M. J. J. Org. Chem. 1989, 54, 2759-2762 and references cited therein. Gundersen, L. L.; Benneche, T.; Rise, F.; Gogoll, A.; Undheim, K. Acta Chem. Scand. 1992, 46, 761-771. Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327-9343. Shibasaki, M.; Nukui, S.; Mori, M. Chem. Lett. 1991, 1791-1800.
10. Trost, B. M.; Hung, M.-H. J. Am. Chem. Soc. 1984, 106, 6837.
11. For an exception see: Trost, B. M.; Krische, M. J.; Radinov, R.; Zanoni, G. J. Am. Chem. Soc. 1996, 118, 6297-6298 and references therein.
12. Trost, B. M.; Verhoeven, T. R.; Fortunak, J. M. Tetrahedron. Lett. 1979, 20, 2301-2304. Matsushita, H.; Negishi, E. J. Chem. Soc., Chem. Commun. 1982, 1982, 160-161. Negishi, E.; John, R. A. J. Org. Chem. 1983, 48, 4098-4102. Byström, S. E.; Aslanian, R.; Bäckvall, J. E. Tetrahedron Lett. 1985, 26, 1749-1752. Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143-1145. Tsuda, T.; Okada, M.; Nishi, S.; Seagusa, T. J. Org. Chem. 1986, 51, 421-426. Murahashi, S. I.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292-3303. Tamaru, Y.; Tanaka, A.; Yasui, K.; Goto, S.; Tanaka, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 787-789. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1996, 118, 235-236.
13. Trost, B. M.; Verhoeven, T. R.; Fortunak, J. M. Tetrahedron. Lett. 1979, 20, 2301-2304. Matsushita, H.; Negishi, E. J. Chem. Soc., Chem. Commun. 1982, 1982, 160-161. Negishi, E.; John, R. A. J. Org. Chem. 1983, 48, 4098-4102. Byström, S. E.; Aslanian, R.; Bäckvall, J. E. Tetrahedron Lett. 1985, 26, 1749-1752. Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143-1145. Tsuda, T.; Okada, M.; Nishi, S.; Seagusa, T. J. Org. Chem. 1986, 51, 421-426. Murahashi, S. I.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292-3303. Tamaru, Y.; Tanaka, A.; Yasui, K.; Goto, S.; Tanaka, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 787-789. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1996, 118, 235-236.
14. Trost, B. M.; Verhoeven, T. R.; Fortunak, J. M. Tetrahedron. Lett. 1979, 20, 2301-2304. Matsushita, H.; Negishi, E. J. Chem. Soc., Chem. Commun. 1982, 1982, 160-161. Negishi, E.; John, R. A. J. Org. Chem. 1983, 48, 4098-4102. Byström, S. E.; Aslanian, R.; Bäckvall, J. E. Tetrahedron Lett. 1985, 26, 1749-1752. Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143-1145. Tsuda, T.; Okada, M.; Nishi, S.; Seagusa, T. J. Org. Chem. 1986, 51, 421-426. Murahashi, S. I.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292-3303. Tamaru, Y.; Tanaka, A.; Yasui, K.; Goto, S.; Tanaka, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 787-789. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1996, 118, 235-236.
15. Trost, B. M.; Verhoeven, T. R.; Fortunak, J. M. Tetrahedron. Lett. 1979, 20, 2301-2304. Matsushita, H.; Negishi, E. J. Chem. Soc., Chem. Commun. 1982, 1982, 160-161. Negishi, E.; John, R. A. J. Org. Chem. 1983, 48, 4098-4102. Byström, S. E.; Aslanian, R.; Bäckvall, J. E. Tetrahedron Lett. 1985, 26, 1749-1752. Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143-1145. Tsuda, T.; Okada, M.; Nishi, S.; Seagusa, T. J. Org. Chem. 1986, 51, 421-426. Murahashi, S. I.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292-3303. Tamaru, Y.; Tanaka, A.; Yasui, K.; Goto, S.; Tanaka, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 787-789. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1996, 118, 235-236.
16. Trost, B. M.; Verhoeven, T. R.; Fortunak, J. M. Tetrahedron. Lett. 1979, 20, 2301-2304. Matsushita, H.; Negishi, E. J. Chem. Soc., Chem. Commun. 1982, 1982, 160-161. Negishi, E.; John, R. A. J. Org. Chem. 1983, 48, 4098-4102. Byström, S. E.; Aslanian, R.; Bäckvall, J. E. Tetrahedron Lett. 1985, 26, 1749-1752. Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143-1145. Tsuda, T.; Okada, M.; Nishi, S.; Seagusa, T. J. Org. Chem. 1986, 51, 421-426. Murahashi, S. I.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292-3303. Tamaru, Y.; Tanaka, A.; Yasui, K.; Goto, S.; Tanaka, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 787-789. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1996, 118, 235-236.
17. Trost, B. M.; Verhoeven, T. R.; Fortunak, J. M. Tetrahedron. Lett. 1979, 20, 2301-2304. Matsushita, H.; Negishi, E. J. Chem. Soc., Chem. Commun. 1982, 1982, 160-161. Negishi, E.; John, R. A. J. Org. Chem. 1983, 48, 4098-4102. Byström, S. E.; Aslanian, R.; Bäckvall, J. E. Tetrahedron Lett. 1985, 26, 1749-1752. Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143-1145. Tsuda, T.; Okada, M.; Nishi, S.; Seagusa, T. J. Org. Chem. 1986, 51, 421-426. Murahashi, S. I.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292-3303. Tamaru, Y.; Tanaka, A.; Yasui, K.; Goto, S.; Tanaka, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 787-789. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1996, 118, 235-236.
18. Trost, B. M.; Verhoeven, T. R.; Fortunak, J. M. Tetrahedron. Lett. 1979, 20, 2301-2304. Matsushita, H.; Negishi, E. J. Chem. Soc., Chem. Commun. 1982, 1982, 160-161. Negishi, E.; John, R. A. J. Org. Chem. 1983, 48, 4098-4102. Byström, S. E.; Aslanian, R.; Bäckvall, J. E. Tetrahedron Lett. 1985, 26, 1749-1752. Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143-1145. Tsuda, T.; Okada, M.; Nishi, S.; Seagusa, T. J. Org. Chem. 1986, 51, 421-426. Murahashi, S. I.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292-3303. Tamaru, Y.; Tanaka, A.; Yasui, K.; Goto, S.; Tanaka, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 787-789. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1996, 118, 235-236.
19. Trost, B. M.; Verhoeven, T. R.; Fortunak, J. M. Tetrahedron. Lett. 1979, 20, 2301-2304. Matsushita, H.; Negishi, E. J. Chem. Soc., Chem. Commun. 1982, 1982, 160-161. Negishi, E.; John, R. A. J. Org. Chem. 1983, 48, 4098-4102. Byström, S. E.; Aslanian, R.; Bäckvall, J. E. Tetrahedron Lett. 1985, 26, 1749-1752. Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143-1145. Tsuda, T.; Okada, M.; Nishi, S.; Seagusa, T. J. Org. Chem. 1986, 51, 421-426. Murahashi, S. I.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292-3303. Tamaru, Y.; Tanaka, A.; Yasui, K.; Goto, S.; Tanaka, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 787-789. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1996, 118, 235-236.
20. Trost, B. M.; Verhoeven, T. R.; Fortunak, J. M. Tetrahedron. Lett. 1979, 20, 2301-2304. Matsushita, H.; Negishi, E. J. Chem. Soc., Chem. Commun. 1982, 1982, 160-161. Negishi, E.; John, R. A. J. Org. Chem. 1983, 48, 4098-4102. Byström, S. E.; Aslanian, R.; Bäckvall, J. E. Tetrahedron Lett. 1985, 26, 1749-1752. Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143-1145. Tsuda, T.; Okada, M.; Nishi, S.; Seagusa, T. J. Org. Chem. 1986, 51, 421-426. Murahashi, S. I.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292-3303. Tamaru, Y.; Tanaka, A.; Yasui, K.; Goto, S.; Tanaka, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 787-789. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1996, 118, 235-236.
21. Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1980, 102, 4730-4743. Dimethyl sodiomalonate is often the nucleophile of choice when testing π-allyl palladium chemistry, presumably because it is highly reactive and adds irreversibly. Heteroatom nucleophiles may be more reactive than malonate, but they react reversibly. For an example, see: Trost, B. M.; Organ, M. G. J. Am. Chem. Soc. 1994, 116, 10320-10321.
22. Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1980, 102, 4730-4743. Dimethyl sodiomalonate is often the nucleophile of choice when testing π-allyl palladium chemistry, presumably because it is highly reactive and adds irreversibly. Heteroatom nucleophiles may be more reactive than malonate, but they react reversibly. For an example, see: Trost, B. M.; Organ, M. G. J. Am. Chem. Soc. 1994, 116, 10320-10321.
23. For a preliminary account of this work see: Aggarwal, V. K.; Monteiro, N.; Tarver, G. J.; Lindell, S. D. J. Org. Chem. 1996, 61, 1192-1193.
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25. Simple lactone see: Larock, R. C.; Hightower, T. R. J. Org. Chem. 1993, 58, 5298-5300 and references cited therein. For its preparation in optically pure form see: (a) Via norbornenone: Le Drian, C.; Greene, A. E. J. Am. Chem. Soc. 1982, 104, 5473-5483 and references cited therein. (b) Via iodo lactone: Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1193-1202.
26. Simple lactone see: Larock, R. C.; Hightower, T. R. J. Org. Chem. 1993, 58, 5298-5300 and references cited therein. For its preparation in optically pure form see: (a) Via norbornenone: Le Drian, C.; Greene, A. E. J. Am. Chem. Soc. 1982, 104, 5473-5483 and references cited therein. (b) Via iodo lactone: Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1193-1202.
27. Simple lactone see: Larock, R. C.; Hightower, T. R. J. Org. Chem. 1993, 58, 5298-5300 and references cited therein. For its preparation in optically pure form see: (a) Via norbornenone: Le Drian, C.; Greene, A. E. J. Am. Chem. Soc. 1982, 104, 5473-5483 and references cited therein. (b) Via iodo lactone: Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1193-1202.
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