Palladium(II) catalyst systems for the addition of boronic acids to bicyclic alkenes: New scope and reactivity

Organic Letters

Volumn 5, Issue 20, 2003, Pages 3695-3698

  Lautens, Mark ^a   Dockendorff, Chris ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; BORONIC ACID DERIVATIVE; PALLADIUM;

ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; METHODOLOGY; REACTION ANALYSIS; RING OPENING;

EID: 0142011110     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035369i     Document Type: Article

References (43)

1. For a recent review, see: Alexakis, A.; Benhaim, C. Eur. J. Org. Chem 2002, 19, 3221.
2. For a recent review, see: Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
3. See for example: (a) Trost, B. M.; Lee, C. In Catalytic Asymmetric Synthesis, 4th ed.; Ojima, I, Ed.; Wiley-VCH: New York, 2000; pp 593-649. (b) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E., Ed.; Springer: Heidelberg, 1999; pp 833-866. (c) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
4. See for example: (a) Trost, B. M.; Lee, C. In Catalytic Asymmetric Synthesis, 4th ed.; Ojima, I, Ed.; Wiley-VCH: New York, 2000; pp 593649. (b) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E., Ed.; Springer: Heidelberg, 1999; pp 833-866. (c) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
5. See for example: (a) Trost, B. M.; Lee, C. In Catalytic Asymmetric Synthesis, 4th ed.; Ojima, I, Ed.; Wiley-VCH: New York, 2000; pp 593649. (b) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E., Ed.; Springer: Heidelberg, 1999; pp 833-866. (c) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
6. Our progress in this area has been reviewed recently: Lautens, M.; Fagnou, K.; Hiebert, S. Acc. Chem. Res. 2003, 36, 48.
7. (a) Lautens, M.; Dockendorff, C.; Fagnou, K.; Malicki, A. Org. Lett. 2002, 4, 1311. A racemic version was also reported:
8. (b) Murakami, M.; Igawa, H. Chem. Commun.. 2002, 390.
9. Deuterium labeling studies and characterizations of the oligomeric products demonstrate that rhodium catalysts can promote C-H activation reactions from carbometalated intermediates, leading to undesired products. These results will be presented in a forthcoming full paper.
10. An April 2003 SciFinder (http://www.cas.org/SCIFINDER/) search of reactions with furan- and thiophene-3-boron species yielded one example from the literature: the rhodium-catalyzed conjugate addition of thiophene-3- tetrafluoroborate to cyclohexenone: Batey, R. A.; Thadani, A. N.; Smil, D. V. Org. Lett. 1999, 1, 1683.
11. (a) Lautens, M.; Hiebert, S.; Renaud, J.-L. J. Am. Chem. Soc. 2000, 122, 1804.
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14. For reviews of the Suzuki reaction, see: (a) Suzuki, A.; Miyaura, N. Chem. Rev. 1995, 95, 2457. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147. (c) Danishefsky, S. J.; Chemler, S. R.; Trauner, D. Angew. Chem., Int. Ed. Eng. 2001, 40, 4544. (d) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
15. For reviews of the Suzuki reaction, see: (a) Suzuki, A.; Miyaura, N. Chem. Rev. 1995, 95, 2457. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147. (c) Danishefsky, S. J.; Chemler, S. R.; Trauner, D. Angew. Chem., Int. Ed. Eng. 2001, 40, 4544. (d) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
16. For reviews of the Suzuki reaction, see: (a) Suzuki, A.; Miyaura, N. Chem. Rev. 1995, 95, 2457. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147. (c) Danishefsky, S. J.; Chemler, S. R.; Trauner, D. Angew. Chem., Int. Ed. Eng. 2001, 40, 4544. (d) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
17. For reviews of the Suzuki reaction, see: (a) Suzuki, A.; Miyaura, N. Chem. Rev. 1995, 95, 2457. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147. (c) Danishefsky, S. J.; Chemler, S. R.; Trauner, D. Angew. Chem., Int. Ed. Eng. 2001, 40, 4544. (d) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
18. It should be noted that during the preparation of this manuscript, the Pd(II)-catalyzed conjugate addition of organoboronic acids was reported by Miyaura and co-workers: Miyaura, N.; Nishikata, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2003, 42, 2768.
19. For other ring-opening syntheses of compound 2aa, see refs 5 and 21 and also: (a) Fiaud, J.-C.; Moinet, C. Tetrahedron Lett. 1995, 36, 2051. (b) Kosugi, M.; Fugami, K.; Hagiwara, S.; Oda, H. Synlett 1998, 477. (c) Nakamura, M.; Nakamura, E.; Matsuo, K.; Inoue, T. Org. Lett. 2003, 5, 1373.
20. For other ring-opening syntheses of compound 2aa, see refs 5 and 21 and also: (a) Fiaud, J.-C.; Moinet, C. Tetrahedron Lett. 1995, 36, 2051. (b) Kosugi, M.; Fugami, K.; Hagiwara, S.; Oda, H. Synlett 1998, 477. (c) Nakamura, M.; Nakamura, E.; Matsuo, K.; Inoue, T. Org. Lett. 2003, 5, 1373.
21. For other ring-opening syntheses of compound 2aa, see refs 5 and 21 and also: (a) Fiaud, J.-C.; Moinet, C. Tetrahedron Lett. 1995, 36, 2051. (b) Kosugi, M.; Fugami, K.; Hagiwara, S.; Oda, H. Synlett 1998, 477. (c) Nakamura, M.; Nakamura, E.; Matsuo, K.; Inoue, T. Org. Lett. 2003, 5, 1373.
22. Generally, addition of carbon-centered nucleophiles gives cis ring-opened products; however, Cu(I)-catalyzed ring-openings of 1a have recently been reported giving predominantly trans products: (a) Feringa, B. L.; Pineschi, M.; Bertozzi, F.; Macchia, F.; Arnold, L. A.; Minnaard, A. J. Org. Lett. 2002, 4, 2703. (b) Carretero, J. C.; Arrayás, R. G.; Cabrera, S. Org. Lett. 2003, 5, 1333.
23. Generally, addition of carbon-centered nucleophiles gives cis ring-opened products; however, Cu(I)-catalyzed ring-openings of 1a have recently been reported giving predominantly trans products: (a) Feringa, B. L.; Pineschi, M.; Bertozzi, F.; Macchia, F.; Arnold, L. A.; Minnaard, A. J. Org. Lett. 2002, 4, 2703. (b) Carretero, J. C.; Arrayás, R. G.; Cabrera, S. Org. Lett. 2003, 5, 1333.
24. 2 both failed to catalyze any reaction of 1a under the optimized conditions given in Table 2 (5 mol % catalyst).
25. See Supporting Information for complete details.
26. 3, and KOH.
27. Use of methanol with Rh(I) catalysts leads to exclusive ring-opening with methanol as a nucleophile; no such products are observed with Pd(II) catalysts.
28. 2 system (ref 5a).
29. Low enantioselectivites (<30%) have been observed in a preliminary screening of chiral ligands in the ring opening of 3a with phenylboronic acid.
30. See Supporting Information for full details.
31. (a) Synthesis: Strukul, G.; Gavagnin, R.; Cataldo, M.; Pinna, F. Organometallics 1998, 17, 661.
32. (b) Characterization: Housecroft, C. E.; Rheingold, A. L.; Shaykh, B. A. M.; Haggerty, B. S. Inorg. Chem. 1991, 30, 125.
33. Ni- and Pd-catalyzed reductive ring-opening of azabicyclic alkenes with aryl halides has been reported by Cheng and co-workers: (a) Cheng, C.-H.; Feng, C.-C.; Nandi, M.; Sambaiah, T. J. Org. Chem. 1999, 64, 3538. (b) Cheng, C.-H.; Duan, J.-P. Organometallics 1995, 14, 1608. (c) Cheng, C.-H.; Duan, J.-P. Tetrahedron Lett. 1993, 34, 4019.
34. Ni- and Pd-catalyzed reductive ring-opening of azabicyclic alkenes with aryl halides has been reported by Cheng and co-workers: (a) Cheng, C.-H.; Feng, C.-C.; Nandi, M.; Sambaiah, T. J. Org. Chem. 1999, 64, 3538. (b) Cheng, C.-H.; Duan, J.-P. Organometallics 1995, 14, 1608. (c) Cheng, C.-H.; Duan, J.-P. Tetrahedron Lett. 1993, 34, 4019.
35. Ni- and Pd-catalyzed reductive ring-opening of azabicyclic alkenes with aryl halides has been reported by Cheng and co-workers: (a) Cheng, C.-H.; Feng, C.-C.; Nandi, M.; Sambaiah, T. J. Org. Chem. 1999, 64, 3538. (b) Cheng, C.-H.; Duan, J.-P. Organometallics 1995, 14, 1608. (c) Cheng, C.-H.; Duan, J.-P. Tetrahedron Lett. 1993, 34, 4019.
36. 3 catalyst system: see ref 5b.
37. As measured by HPLC.
38. Isolated yields in oxabicycle ring-opening reactions are generally lower than the analogous azabicycle reactions due to their decreased stability (elimination of water) relative to the Boc-protected amino products.
39. Synthesis: Sodeoka, M.; Fujii, A.; Hagiwara, E. J. Am. Chem. Soc. 1999, 121, 5450.
40. For more detailed discussions of this mechanism, see ref 8c.
41. 2 (1 mol %).
42. Lautens, M.; Rovis. T. Tetrahedron 1999, 55, 8967.
43. Lautens, M.; Fagnou, K.; Zunic, V. Org. Lett. 2002, 4, 3465.