Coupled organolanthanide-catalyzed C-N/C-C bond formation processes. Efficient regiospecific assembly of pyrrolizidine and indolizidine skeletons in a single catalytic reaction

Journal of the American Chemical Society

Volumn 118, Issue 3, 1996, Pages 707-708

  Li, Yanwu ^a   Marks, Tobin J ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLIZIDINE DERIVATIVE; PYRROLIZIDINE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030034297     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja952433l     Document Type: Article

References (39)

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2. Alkene insertions involving alkyls: (a) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283-362 and references therein. (b) Jeske, G.; Lauke, H.; Mauermann, H.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8091-8103. (c) Watson, P. L.; Parshall, G. W. Acc. Chem. Res. 1985, 18, 51-55. (d) den Haan, K. H.; de Boer, J. L.; Teuben, J. H.; Spek, A. L.; Kajic-Prodic, B.; Hays, G. R.; Huis, R. Organometallics 1986, 5, 1726-1733. (e) Molander, G. A.; Hoberg, J. O. J. Am. Chem. Soc. 1992, 114, 3123-3124. (f) Yang, X.; Seyam, A. M.; Fu, P.-F.; Marks, T. J. Macromolecules 1994, 27, 4625-4626. (g) Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 117, 4415-4416.
3. Alkene insertions involving alkyls: (a) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283-362 and references therein. (b) Jeske, G.; Lauke, H.; Mauermann, H.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8091-8103. (c) Watson, P. L.; Parshall, G. W. Acc. Chem. Res. 1985, 18, 51-55. (d) den Haan, K. H.; de Boer, J. L.; Teuben, J. H.; Spek, A. L.; Kajic-Prodic, B.; Hays, G. R.; Huis, R. Organometallics 1986, 5, 1726-1733. (e) Molander, G. A.; Hoberg, J. O. J. Am. Chem. Soc. 1992, 114, 3123-3124. (f) Yang, X.; Seyam, A. M.; Fu, P.-F.; Marks, T. J. Macromolecules 1994, 27, 4625-4626. (g) Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 117, 4415-4416.
4. Alkene insertions involving alkyls: (a) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283-362 and references therein. (b) Jeske, G.; Lauke, H.; Mauermann, H.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8091-8103. (c) Watson, P. L.; Parshall, G. W. Acc. Chem. Res. 1985, 18, 51-55. (d) den Haan, K. H.; de Boer, J. L.; Teuben, J. H.; Spek, A. L.; Kajic-Prodic, B.; Hays, G. R.; Huis, R. Organometallics 1986, 5, 1726-1733. (e) Molander, G. A.; Hoberg, J. O. J. Am. Chem. Soc. 1992, 114, 3123-3124. (f) Yang, X.; Seyam, A. M.; Fu, P.-F.; Marks, T. J. Macromolecules 1994, 27, 4625-4626. (g) Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 117, 4415-4416.
5. Alkene insertions involving alkyls: (a) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283-362 and references therein. (b) Jeske, G.; Lauke, H.; Mauermann, H.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8091-8103. (c) Watson, P. L.; Parshall, G. W. Acc. Chem. Res. 1985, 18, 51-55. (d) den Haan, K. H.; de Boer, J. L.; Teuben, J. H.; Spek, A. L.; Kajic-Prodic, B.; Hays, G. R.; Huis, R. Organometallics 1986, 5, 1726-1733. (e) Molander, G. A.; Hoberg, J. O. J. Am. Chem. Soc. 1992, 114, 3123-3124. (f) Yang, X.; Seyam, A. M.; Fu, P.-F.; Marks, T. J. Macromolecules 1994, 27, 4625-4626. (g) Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 117, 4415-4416.
6. Alkene insertions involving alkyls: (a) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283-362 and references therein. (b) Jeske, G.; Lauke, H.; Mauermann, H.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8091-8103. (c) Watson, P. L.; Parshall, G. W. Acc. Chem. Res. 1985, 18, 51-55. (d) den Haan, K. H.; de Boer, J. L.; Teuben, J. H.; Spek, A. L.; Kajic-Prodic, B.; Hays, G. R.; Huis, R. Organometallics 1986, 5, 1726-1733. (e) Molander, G. A.; Hoberg, J. O. J. Am. Chem. Soc. 1992, 114, 3123-3124. (f) Yang, X.; Seyam, A. M.; Fu, P.-F.; Marks, T. J. Macromolecules 1994, 27, 4625-4626. (g) Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 117, 4415-4416.
7. Alkene insertions involving alkyls: (a) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283-362 and references therein. (b) Jeske, G.; Lauke, H.; Mauermann, H.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8091-8103. (c) Watson, P. L.; Parshall, G. W. Acc. Chem. Res. 1985, 18, 51-55. (d) den Haan, K. H.; de Boer, J. L.; Teuben, J. H.; Spek, A. L.; Kajic-Prodic, B.; Hays, G. R.; Huis, R. Organometallics 1986, 5, 1726-1733. (e) Molander, G. A.; Hoberg, J. O. J. Am. Chem. Soc. 1992, 114, 3123-3124. (f) Yang, X.; Seyam, A. M.; Fu, P.-F.; Marks, T. J. Macromolecules 1994, 27, 4625-4626. (g) Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 117, 4415-4416.
8. Alkene insertions involving heteroatoms: (a) Giardello, M. A.; Conticello, V. P.; Brard, L.; Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10241-10254. (b) Giardello, M. A.; King, W. A.; Nolan, S. P.; Porchia, M.; Sishta, C.; Marks, T. J. In Energetics of Organometallic Species; Martinho Simoes, J. A., Ed.; Kluwer: Dordrecht, 1992; pp 35-51. (c) Gagné, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275-294. (d) Gagné, M. R.; Nolan, S. P.; Marks, T. J. Organometallics 1990, 9, 1716-1718.
9. Alkene insertions involving heteroatoms: (a) Giardello, M. A.; Conticello, V. P.; Brard, L.; Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10241-10254. (b) Giardello, M. A.; King, W. A.; Nolan, S. P.; Porchia, M.; Sishta, C.; Marks, T. J. In Energetics of Organometallic Species; Martinho Simoes, J. A., Ed.; Kluwer: Dordrecht, 1992; pp 35-51. (c) Gagné, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275-294. (d) Gagné, M. R.; Nolan, S. P.; Marks, T. J. Organometallics 1990, 9, 1716-1718.
10. Alkene insertions involving heteroatoms: (a) Giardello, M. A.; Conticello, V. P.; Brard, L.; Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10241-10254. (b) Giardello, M. A.; King, W. A.; Nolan, S. P.; Porchia, M.; Sishta, C.; Marks, T. J. In Energetics of Organometallic Species; Martinho Simoes, J. A., Ed.; Kluwer: Dordrecht, 1992; pp 35-51. (c) Gagné, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275-294. (d) Gagné, M. R.; Nolan, S. P.; Marks, T. J. Organometallics 1990, 9, 1716-1718.
11. Alkene insertions involving heteroatoms: (a) Giardello, M. A.; Conticello, V. P.; Brard, L.; Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10241-10254. (b) Giardello, M. A.; King, W. A.; Nolan, S. P.; Porchia, M.; Sishta, C.; Marks, T. J. In Energetics of Organometallic Species; Martinho Simoes, J. A., Ed.; Kluwer: Dordrecht, 1992; pp 35-51. (c) Gagné, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275-294. (d) Gagné, M. R.; Nolan, S. P.; Marks, T. J. Organometallics 1990, 9, 1716-1718.
12. Alkyne insertions involving alkyls: (a) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980-1986 and references therein.
13. (b) Heeres, H. J.; Meetsma, A.; Teuben, J. H.; Rogers, R. D. Organometallics 1989, 8, 2637-2646.
14. Alkyne insertions involving heteroatoms: (a) Li, Y.; Fu. P.-F.; Marks, T. J. Organometallics 1994, 13, 439-440. (b) Li, Y.; Marks. T. J. Abstracts of Papers, 34th National Organic Symposium, ACS Division of Organic Chemistry, Williamsburg, VA, June 1995; American Chemical Society: Washington, DC, 1995; Abstract 44.
15. Alkyne insertions involving heteroatoms: (a) Li, Y.; Fu. P.-F.; Marks, T. J. Organometallics 1994, 13, 439-440. (b) Li, Y.; Marks. T. J. Abstracts of Papers, 34th National Organic Symposium, ACS Division of Organic Chemistry, Williamsburg, VA, June 1995; American Chemical Society: Washington, DC, 1995; Abstract 44.
16. For some leading reviews, see: (a) Robins, D. J. Nat. Prod. Rep. 1994, 11, 613-619 and references therein. (b) Michael, J. P. Nat. Prod. Rep. 1994, 11, 639-657 and references therein. (c) Daly, J. W.; Spande, T. F. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.: Wiley: New York, 1986; Vol. 4, Chapter 1. (d) Mattocks, A. R. Chemistry and Toxicology of Pyrrolizidine Alkaloids: Academic Press: Orlando, 1986. (e) Robins, D. J. Adv. Heterocycl. Chem. 1979, 24, 247-291.
17. For some leading reviews, see: (a) Robins, D. J. Nat. Prod. Rep. 1994, 11, 613-619 and references therein. (b) Michael, J. P. Nat. Prod. Rep. 1994, 11, 639-657 and references therein. (c) Daly, J. W.; Spande, T. F. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.: Wiley: New York, 1986; Vol. 4, Chapter 1. (d) Mattocks, A. R. Chemistry and Toxicology of Pyrrolizidine Alkaloids: Academic Press: Orlando, 1986. (e) Robins, D. J. Adv. Heterocycl. Chem. 1979, 24, 247-291.
18. For some leading reviews, see: (a) Robins, D. J. Nat. Prod. Rep. 1994, 11, 613-619 and references therein. (b) Michael, J. P. Nat. Prod. Rep. 1994, 11, 639-657 and references therein. (c) Daly, J. W.; Spande, T. F. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.: Wiley: New York, 1986; Vol. 4, Chapter 1. (d) Mattocks, A. R. Chemistry and Toxicology of Pyrrolizidine Alkaloids: Academic Press: Orlando, 1986. (e) Robins, D. J. Adv. Heterocycl. Chem. 1979, 24, 247-291.
19. For some leading reviews, see: (a) Robins, D. J. Nat. Prod. Rep. 1994, 11, 613-619 and references therein. (b) Michael, J. P. Nat. Prod. Rep. 1994, 11, 639-657 and references therein. (c) Daly, J. W.; Spande, T. F. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.: Wiley: New York, 1986; Vol. 4, Chapter 1. (d) Mattocks, A. R. Chemistry and Toxicology of Pyrrolizidine Alkaloids: Academic Press: Orlando, 1986. (e) Robins, D. J. Adv. Heterocycl. Chem. 1979, 24, 247-291.
20. For some leading reviews, see: (a) Robins, D. J. Nat. Prod. Rep. 1994, 11, 613-619 and references therein. (b) Michael, J. P. Nat. Prod. Rep. 1994, 11, 639-657 and references therein. (c) Daly, J. W.; Spande, T. F. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.: Wiley: New York, 1986; Vol. 4, Chapter 1. (d) Mattocks, A. R. Chemistry and Toxicology of Pyrrolizidine Alkaloids: Academic Press: Orlando, 1986. (e) Robins, D. J. Adv. Heterocycl. Chem. 1979, 24, 247-291.
21. For representative synthetic approaches, see: (a) Hudlickly, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 937-965 and references therein. (b) Hassner, A.; Rai, K. M. L. In ref 6a, Vol. 2, pp 557-559 and references therein. (c) Shiosaki, K. In ref 6a, Vol. 3, pp 882-885 and references therein. (d) Overman, L. E.; Ricca, D. J. In ref 6a. Vol. 3, pp 1040-1044 and references therein. (e) McGrane, P. L., Livinghouse, T. J. Org. Chem. 1992, 57, 1323-1324 and references therein. (f) Jefford, C. W.; Tang, Q.; Zaslona, A. J. Am. Chem. Soc. 1991, 113, 3513-3518.
22. For representative synthetic approaches, see: (a) Hudlickly, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 937-965 and references therein. (b) Hassner, A.; Rai, K. M. L. In ref 6a, Vol. 2, pp 557-559 and references therein. (c) Shiosaki, K. In ref 6a, Vol. 3, pp 882-885 and references therein. (d) Overman, L. E.; Ricca, D. J. In ref 6a. Vol. 3, pp 1040-1044 and references therein. (e) McGrane, P. L., Livinghouse, T. J. Org. Chem. 1992, 57, 1323-1324 and references therein. (f) Jefford, C. W.; Tang, Q.; Zaslona, A. J. Am. Chem. Soc. 1991, 113, 3513-3518.
23. For representative synthetic approaches, see: (a) Hudlickly, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 937-965 and references therein. (b) Hassner, A.; Rai, K. M. L. In ref 6a, Vol. 2, pp 557-559 and references therein. (c) Shiosaki, K. In ref 6a, Vol. 3, pp 882-885 and references therein. (d) Overman, L. E.; Ricca, D. J. In ref 6a. Vol. 3, pp 1040-1044 and references therein. (e) McGrane, P. L., Livinghouse, T. J. Org. Chem. 1992, 57, 1323-1324 and references therein. (f) Jefford, C. W.; Tang, Q.; Zaslona, A. J. Am. Chem. Soc. 1991, 113, 3513-3518.
24. For representative synthetic approaches, see: (a) Hudlickly, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 937-965 and references therein. (b) Hassner, A.; Rai, K. M. L. In ref 6a, Vol. 2, pp 557-559 and references therein. (c) Shiosaki, K. In ref 6a, Vol. 3, pp 882-885 and references therein. (d) Overman, L. E.; Ricca, D. J. In ref 6a. Vol. 3, pp 1040-1044 and references therein. (e) McGrane, P. L., Livinghouse, T. J. Org. Chem. 1992, 57, 1323-1324 and references therein. (f) Jefford, C. W.; Tang, Q.; Zaslona, A. J. Am. Chem. Soc. 1991, 113, 3513-3518.
25. For representative synthetic approaches, see: (a) Hudlickly, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 937-965 and references therein. (b) Hassner, A.; Rai, K. M. L. In ref 6a, Vol. 2, pp 557-559 and references therein. (c) Shiosaki, K. In ref 6a, Vol. 3, pp 882-885 and references therein. (d) Overman, L. E.; Ricca, D. J. In ref 6a. Vol. 3, pp 1040-1044 and references therein. (e) McGrane, P. L., Livinghouse, T. J. Org. Chem. 1992, 57, 1323-1324 and references therein. (f) Jefford, C. W.; Tang, Q.; Zaslona, A. J. Am. Chem. Soc. 1991, 113, 3513-3518.
26. For representative synthetic approaches, see: (a) Hudlickly, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 937-965 and references therein. (b) Hassner, A.; Rai, K. M. L. In ref 6a, Vol. 2, pp 557-559 and references therein. (c) Shiosaki, K. In ref 6a, Vol. 3, pp 882-885 and references therein. (d) Overman, L. E.; Ricca, D. J. In ref 6a. Vol. 3, pp 1040-1044 and references therein. (e) McGrane, P. L., Livinghouse, T. J. Org. Chem. 1992, 57, 1323-1324 and references therein. (f) Jefford, C. W.; Tang, Q.; Zaslona, A. J. Am. Chem. Soc. 1991, 113, 3513-3518.
27. Communicated in part: Li, Y., Marks, T. J. Abstracts of Papers, 209th National Meeting of the American Chemical Society, Anaheim, CA, Spring 1995; American Chemical Society: Washington, DC, 1995; INOR012.
28. See supporting information for full synthetic details and characterization data for new compounds.
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