Bis(oxazoline) and bis(oxazolinyl)pyridine copper complexes as enantioselective Diels-Alder catalysts: Reaction scope and synthetic applications

Journal of the American Chemical Society

Volumn 121, Issue 33, 1999, Pages 7582-7594

  Evans, David A ^a   Barnes, David M ^a   Johnson, Jeffrey S ^a   Lectka, Thomas ^a   Von Matt, Peter ^a   Miller, Scott J ^a   Murry, Jerry A ^a   Norcross, Roger D ^a   Shaughnessy, Eileen A ^a   Campos, Kevin R ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; COMPLEX FORMATION; SYNTHESIS;

EID: 0033603850     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991191c     Document Type: Article

References (139)

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2. For reviews see: (a) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007-1020. (b) Pindur, U.; Lutz, G.; Otto, C. Chem. Rev. 1993, 93, 741-761. (c) Dias, L. C. J. Braz. Chem. Soc. 1997, 8, 289-332. (d) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763-784. (e) Maruoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 413-440. (f) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1993; pp 212-217. (g) Oh, T.; Reilly, M. Org. Prep. Proced. Int. 1994, 26, 129-158. (h) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92.
3. For reviews see: (a) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007-1020. (b) Pindur, U.; Lutz, G.; Otto, C. Chem. Rev. 1993, 93, 741- 761. (c) Dias, L. C. J. Braz. Chem. Soc. 1997, 8, 289-332. (d) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763-784. (e) Maruoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 413-440. (f) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1993; pp 212-217. (g) Oh, T.; Reilly, M. Org. Prep. Proced. Int. 1994, 26, 129-158. (h) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92.
4. For reviews see: (a) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007-1020. (b) Pindur, U.; Lutz, G.; Otto, C. Chem. Rev. 1993, 93, 741- 761. (c) Dias, L. C. J. Braz. Chem. Soc. 1997, 8, 289-332. (d) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763-784. (e) Maruoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 413-440. (f) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1993; pp 212-217. (g) Oh, T.; Reilly, M. Org. Prep. Proced. Int. 1994, 26, 129-158. (h) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92.
5. For reviews see: (a) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007-1020. (b) Pindur, U.; Lutz, G.; Otto, C. Chem. Rev. 1993, 93, 741- 761. (c) Dias, L. C. J. Braz. Chem. Soc. 1997, 8, 289-332. (d) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763-784. (e) Maruoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 413-440. (f) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1993; pp 212-217. (g) Oh, T.; Reilly, M. Org. Prep. Proced. Int. 1994, 26, 129-158. (h) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92.
6. For reviews see: (a) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007-1020. (b) Pindur, U.; Lutz, G.; Otto, C. Chem. Rev. 1993, 93, 741- 761. (c) Dias, L. C. J. Braz. Chem. Soc. 1997, 8, 289-332. (d) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763-784. (e) Maruoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 413-440. (f) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1993; pp 212-217. (g) Oh, T.; Reilly, M. Org. Prep. Proced. Int. 1994, 26, 129-158. (h) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92.
7. For reviews see: (a) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007-1020. (b) Pindur, U.; Lutz, G.; Otto, C. Chem. Rev. 1993, 93, 741- 761. (c) Dias, L. C. J. Braz. Chem. Soc. 1997, 8, 289-332. (d) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763-784. (e) Maruoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 413-440. (f) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1993; pp 212-217. (g) Oh, T.; Reilly, M. Org. Prep. Proced. Int. 1994, 26, 129-158. (h) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92.
8. For reviews see: (a) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007-1020. (b) Pindur, U.; Lutz, G.; Otto, C. Chem. Rev. 1993, 93, 741- 761. (c) Dias, L. C. J. Braz. Chem. Soc. 1997, 8, 289-332. (d) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763-784. (e) Maruoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 413-440. (f) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1993; pp 212-217. (g) Oh, T.; Reilly, M. Org. Prep. Proced. Int. 1994, 26, 129-158. (h) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92.
9. (a) Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460-6461.
10. (b) Evans, D. A.; Lectka, T.; Miller, S. J. Tetrahedron Lett. 1993, 34, 7027-7030.
11. (c) Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798-800.
12. (d) Previous paper, this issue.
13. For the use of these complexes in Mukaiyama aldol reactions see: (a) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669-685 and references therein. (b) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686-699 and references therein.
14. For the use of these complexes in Mukaiyama aldol reactions see: (a) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669- 685 and references therein. (b) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686-699 and references therein.
15. For the relative effectiveness of chiral Lewis acids derived from Cu-(II) and Zn(II), see: Evans, D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481-7484.
16. Several other catalysts have also been reported to provide good to excellent enantioselectivities in the reactions of cyclopentadiene with 2 and with β-substituted acrylimides (R ≠ H). Al: (a) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Yb, Sc: (b) Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535-4538. (c) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083-4084. (d) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623-11636. (e) Nishida, A.; Yamanaka, M.; Nakagawa, M. Tetrahedron Lett. 1999, 40, 1555-1558. Zr: (f) Jaquith, J. B.; Levy, C. J.; Bondar, G. V.; Wang, S. T.; Collins, S. Organometallics 1998, 17, 914-925 and references therein. Cu: (g) Ghosh, A. K.; Cho, H.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 3687-3691 and references therein. (h) Sagasser, I.; Helmchen, G. Tetrahedron Lett. 1998, 39, 261-264. Ni: (i) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074-3088 and references therein. Zn: (j) Takacs, J. M.; Quincy, D. A.; Shay, W.; Jones, B. E.; Ross, C. R. Tetrahedron: Asymmetry 1997, 8, 3079-3087 and references therein.
17. Several other catalysts have also been reported to provide good to excellent enantioselectivities in the reactions of cyclopentadiene with 2 and with β-substituted acrylimides (R ≠ H). Al: (a) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Yb, Sc: (b) Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535-4538. (c) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083-4084. (d) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623-11636. (e) Nishida, A.; Yamanaka, M.; Nakagawa, M. Tetrahedron Lett. 1999, 40, 1555-1558. Zr: (f) Jaquith, J. B.; Levy, C. J.; Bondar, G. V.; Wang, S. T.; Collins, S. Organometallics 1998, 17, 914-925 and references therein. Cu: (g) Ghosh, A. K.; Cho, H.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 3687-3691 and references therein. (h) Sagasser, I.; Helmchen, G. Tetrahedron Lett. 1998, 39, 261-264. Ni: (i) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074-3088 and references therein. Zn: (j) Takacs, J. M.; Quincy, D. A.; Shay, W.; Jones, B. E.; Ross, C. R. Tetrahedron: Asymmetry 1997, 8, 3079-3087 and references therein.
18. Several other catalysts have also been reported to provide good to excellent enantioselectivities in the reactions of cyclopentadiene with 2 and with β-substituted acrylimides (R ≠ H). Al: (a) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Yb, Sc: (b) Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535-4538. (c) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083-4084. (d) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623-11636. (e) Nishida, A.; Yamanaka, M.; Nakagawa, M. Tetrahedron Lett. 1999, 40, 1555-1558. Zr: (f) Jaquith, J. B.; Levy, C. J.; Bondar, G. V.; Wang, S. T.; Collins, S. Organometallics 1998, 17, 914-925 and references therein. Cu: (g) Ghosh, A. K.; Cho, H.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 3687-3691 and references therein. (h) Sagasser, I.; Helmchen, G. Tetrahedron Lett. 1998, 39, 261-264. Ni: (i) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074-3088 and references therein. Zn: (j) Takacs, J. M.; Quincy, D. A.; Shay, W.; Jones, B. E.; Ross, C. R. Tetrahedron: Asymmetry 1997, 8, 3079-3087 and references therein.
19. Several other catalysts have also been reported to provide good to excellent enantioselectivities in the reactions of cyclopentadiene with 2 and with β-substituted acrylimides (R ≠ H). Al: (a) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Yb, Sc: (b) Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535-4538. (c) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083-4084. (d) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623-11636. (e) Nishida, A.; Yamanaka, M.; Nakagawa, M. Tetrahedron Lett. 1999, 40, 1555-1558. Zr: (f) Jaquith, J. B.; Levy, C. J.; Bondar, G. V.; Wang, S. T.; Collins, S. Organometallics 1998, 17, 914-925 and references therein. Cu: (g) Ghosh, A. K.; Cho, H.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 3687-3691 and references therein. (h) Sagasser, I.; Helmchen, G. Tetrahedron Lett. 1998, 39, 261-264. Ni: (i) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074-3088 and references therein. Zn: (j) Takacs, J. M.; Quincy, D. A.; Shay, W.; Jones, B. E.; Ross, C. R. Tetrahedron: Asymmetry 1997, 8, 3079-3087 and references therein.
20. Several other catalysts have also been reported to provide good to excellent enantioselectivities in the reactions of cyclopentadiene with 2 and with β-substituted acrylimides (R ≠ H). Al: (a) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Yb, Sc: (b) Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535-4538. (c) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083-4084. (d) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623-11636. (e) Nishida, A.; Yamanaka, M.; Nakagawa, M. Tetrahedron Lett. 1999, 40, 1555-1558. Zr: (f) Jaquith, J. B.; Levy, C. J.; Bondar, G. V.; Wang, S. T.; Collins, S. Organometallics 1998, 17, 914-925 and references therein. Cu: (g) Ghosh, A. K.; Cho, H.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 3687-3691 and references therein. (h) Sagasser, I.; Helmchen, G. Tetrahedron Lett. 1998, 39, 261-264. Ni: (i) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074-3088 and references therein. Zn: (j) Takacs, J. M.; Quincy, D. A.; Shay, W.; Jones, B. E.; Ross, C. R. Tetrahedron: Asymmetry 1997, 8, 3079-3087 and references therein.
21. Several other catalysts have also been reported to provide good to excellent enantioselectivities in the reactions of cyclopentadiene with 2 and with β-substituted acrylimides (R ≠ H). Al: (a) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Yb, Sc: (b) Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535-4538. (c) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083-4084. (d) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623-11636. (e) Nishida, A.; Yamanaka, M.; Nakagawa, M. Tetrahedron Lett. 1999, 40, 1555-1558. Zr: (f) Jaquith, J. B.; Levy, C. J.; Bondar, G. V.; Wang, S. T.; Collins, S. Organometallics 1998, 17, 914-925 and references therein. Cu: (g) Ghosh, A. K.; Cho, H.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 3687-3691 and references therein. (h) Sagasser, I.; Helmchen, G. Tetrahedron Lett. 1998, 39, 261-264. Ni: (i) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074-3088 and references therein. Zn: (j) Takacs, J. M.; Quincy, D. A.; Shay, W.; Jones, B. E.; Ross, C. R. Tetrahedron: Asymmetry 1997, 8, 3079-3087 and references therein.
22. Several other catalysts have also been reported to provide good to excellent enantioselectivities in the reactions of cyclopentadiene with 2 and with β-substituted acrylimides (R ≠ H). Al: (a) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Yb, Sc: (b) Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535-4538. (c) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083-4084. (d) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623-11636. (e) Nishida, A.; Yamanaka, M.; Nakagawa, M. Tetrahedron Lett. 1999, 40, 1555-1558. Zr: (f) Jaquith, J. B.; Levy, C. J.; Bondar, G. V.; Wang, S. T.; Collins, S. Organometallics 1998, 17, 914-925 and references therein. Cu: (g) Ghosh, A. K.; Cho, H.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 3687-3691 and references therein. (h) Sagasser, I.; Helmchen, G. Tetrahedron Lett. 1998, 39, 261-264. Ni: (i) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074-3088 and references therein. Zn: (j) Takacs, J. M.; Quincy, D. A.; Shay, W.; Jones, B. E.; Ross, C. R. Tetrahedron: Asymmetry 1997, 8, 3079-3087 and references therein.
23. Several other catalysts have also been reported to provide good to excellent enantioselectivities in the reactions of cyclopentadiene with 2 and with β-substituted acrylimides (R ≠ H). Al: (a) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Yb, Sc: (b) Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535-4538. (c) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083-4084. (d) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623-11636. (e) Nishida, A.; Yamanaka, M.; Nakagawa, M. Tetrahedron Lett. 1999, 40, 1555-1558. Zr: (f) Jaquith, J. B.; Levy, C. J.; Bondar, G. V.; Wang, S. T.; Collins, S. Organometallics 1998, 17, 914-925 and references therein. Cu: (g) Ghosh, A. K.; Cho, H.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 3687-3691 and references therein. (h) Sagasser, I.; Helmchen, G. Tetrahedron Lett. 1998, 39, 261-264. Ni: (i) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074-3088 and references therein. Zn: (j) Takacs, J. M.; Quincy, D. A.; Shay, W.; Jones, B. E.; Ross, C. R. Tetrahedron: Asymmetry 1997, 8, 3079-3087 and references therein.
24. Several other catalysts have also been reported to provide good to excellent enantioselectivities in the reactions of cyclopentadiene with 2 and with β-substituted acrylimides (R ≠ H). Al: (a) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Yb, Sc: (b) Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535-4538. (c) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083-4084. (d) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623-11636. (e) Nishida, A.; Yamanaka, M.; Nakagawa, M. Tetrahedron Lett. 1999, 40, 1555-1558. Zr: (f) Jaquith, J. B.; Levy, C. J.; Bondar, G. V.; Wang, S. T.; Collins, S. Organometallics 1998, 17, 914-925 and references therein. Cu: (g) Ghosh, A. K.; Cho, H.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 3687-3691 and references therein. (h) Sagasser, I.; Helmchen, G. Tetrahedron Lett. 1998, 39, 261-264. Ni: (i) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074-3088 and references therein. Zn: (j) Takacs, J. M.; Quincy, D. A.; Shay, W.; Jones, B. E.; Ross, C. R. Tetrahedron: Asymmetry 1997, 8, 3079-3087 and references therein.
25. Several other catalysts have also been reported to provide good to excellent enantioselectivities in the reactions of cyclopentadiene with 2 and with β-substituted acrylimides (R ≠ H). Al: (a) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Yb, Sc: (b) Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535-4538. (c) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083-4084. (d) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623-11636. (e) Nishida, A.; Yamanaka, M.; Nakagawa, M. Tetrahedron Lett. 1999, 40, 1555-1558. Zr: (f) Jaquith, J. B.; Levy, C. J.; Bondar, G. V.; Wang, S. T.; Collins, S. Organometallics 1998, 17, 914-925 and references therein. Cu: (g) Ghosh, A. K.; Cho, H.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 3687-3691 and references therein. (h) Sagasser, I.; Helmchen, G. Tetrahedron Lett. 1998, 39, 261-264. Ni: (i) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074-3088 and references therein. Zn: (j) Takacs, J. M.; Quincy, D. A.; Shay, W.; Jones, B. E.; Ross, C. R. Tetrahedron: Asymmetry 1997, 8, 3079-3087 and references therein.
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37. For recent examples, see: (a) Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502-5503. (b) Bruin, M. E.; Kundig, E. P. Chem. Commun. 1998, 2635-2636. (c) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. (d) Yamamoto, H.; Ishihara, K. J. Am. Chem. Soc. 1994, 116, 1561-1562. (e) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049-3050. (f) Reference 5g. (g) Ishihara, K.; Gao, Q. Z.; Yamamoto, H. J. Org. Chem. 1993, 58, 6917-6919 and references therein. (h) Corey, E. J.; Guzman-Perez, A.; Loh, T. P. J. Am. Chem. Soc. 1994, 116, 3611-3612 and references therein.
38. For recent examples, see: (a) Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502-5503. (b) Bruin, M. E.; Kundig, E. P. Chem. Commun. 1998, 2635-2636. (c) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. (d) Yamamoto, H.; Ishihara, K. J. Am. Chem. Soc. 1994, 116, 1561-1562. (e) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049-3050. (f) Reference 5g. (g) Ishihara, K.; Gao, Q. Z.; Yamamoto, H. J. Org. Chem. 1993, 58, 6917-6919 and references therein. (h) Corey, E. J.; Guzman-Perez, A.; Loh, T. P. J. Am. Chem. Soc. 1994, 116, 3611-3612 and references therein.
39. For recent examples, see: (a) Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502-5503. (b) Bruin, M. E.; Kundig, E. P. Chem. Commun. 1998, 2635-2636. (c) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. (d) Yamamoto, H.; Ishihara, K. J. Am. Chem. Soc. 1994, 116, 1561-1562. (e) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049-3050. (f) Reference 5g. (g) Ishihara, K.; Gao, Q. Z.; Yamamoto, H. J. Org. Chem. 1993, 58, 6917-6919 and references therein. (h) Corey, E. J.; Guzman-Perez, A.; Loh, T. P. J. Am. Chem. Soc. 1994, 116, 3611-3612 and references therein.
40. For recent examples, see: (a) Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502-5503. (b) Bruin, M. E.; Kundig, E. P. Chem. Commun. 1998, 2635-2636. (c) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. (d) Yamamoto, H.; Ishihara, K. J. Am. Chem. Soc. 1994, 116, 1561-1562. (e) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049-3050. (f) Reference 5g. (g) Ishihara, K.; Gao, Q. Z.; Yamamoto, H. J. Org. Chem. 1993, 58, 6917-6919 and references therein. (h) Corey, E. J.; Guzman-Perez, A.; Loh, T. P. J. Am. Chem. Soc. 1994, 116, 3611-3612 and references therein.
41. For recent examples, see: (a) Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502-5503. (b) Bruin, M. E.; Kundig, E. P. Chem. Commun. 1998, 2635-2636. (c) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. (d) Yamamoto, H.; Ishihara, K. J. Am. Chem. Soc. 1994, 116, 1561-1562. (e) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049-3050. (f) Reference 5g. (g) Ishihara, K.; Gao, Q. Z.; Yamamoto, H. J. Org. Chem. 1993, 58, 6917-6919 and references therein. (h) Corey, E. J.; Guzman-Perez, A.; Loh, T. P. J. Am. Chem. Soc. 1994, 116, 3611-3612 and references therein.
42. For recent examples, see: (a) Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502-5503. (b) Bruin, M. E.; Kundig, E. P. Chem. Commun. 1998, 2635-2636. (c) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. (d) Yamamoto, H.; Ishihara, K. J. Am. Chem. Soc. 1994, 116, 1561-1562. (e) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049-3050. (f) Reference 5g. (g) Ishihara, K.; Gao, Q. Z.; Yamamoto, H. J. Org. Chem. 1993, 58, 6917-6919 and references therein. (h) Corey, E. J.; Guzman-Perez, A.; Loh, T. P. J. Am. Chem. Soc. 1994, 116, 3611-3612 and references therein.
43. For recent examples, see: (a) Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502-5503. (b) Bruin, M. E.; Kundig, E. P. Chem. Commun. 1998, 2635-2636. (c) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. (d) Yamamoto, H.; Ishihara, K. J. Am. Chem. Soc. 1994, 116, 1561-1562. (e) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049-3050. (f) Reference 5g. (g) Ishihara, K.; Gao, Q. Z.; Yamamoto, H. J. Org. Chem. 1993, 58, 6917-6919 and references therein. (h) Corey, E. J.; Guzman-Perez, A.; Loh, T. P. J. Am. Chem. Soc. 1994, 116, 3611-3612 and references therein.
44. For recent examples, see: (a) Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502-5503. (b) Bruin, M. E.; Kundig, E. P. Chem. Commun. 1998, 2635-2636. (c) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. (d) Yamamoto, H.; Ishihara, K. J. Am. Chem. Soc. 1994, 116, 1561-1562. (e) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049-3050. (f) Reference 5g. (g) Ishihara, K.; Gao, Q. Z.; Yamamoto, H. J. Org. Chem. 1993, 58, 6917-6919 and references therein. (h) Corey, E. J.; Guzman-Perez, A.; Loh, T. P. J. Am. Chem. Soc. 1994, 116, 3611-3612 and references therein.
45. (a) References 8 and 9e.
46. (b) Furuta, K.; Kanematsu, A.; Yamamoto, H. Tetrahedron Lett. 1989, 30, 7231-7232.
47. A portion of this work has been communicated. (a) Reference 2c. (b) Evans, D. A.; Barnes, D. M. Tetrahedron Lett. 1997, 38, 57-58. (c) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786-787. (d) Evans, D. A.; Shaughnessy, E. A.; Barnes, D. M. Tetrahedron Lett. 1997, 38, 3193-3194.
48. A portion of this work has been communicated. (a) Reference 2c. (b) Evans, D. A.; Barnes, D. M. Tetrahedron Lett. 1997, 38, 57-58. (c) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786-787. (d) Evans, D. A.; Shaughnessy, E. A.; Barnes, D. M. Tetrahedron Lett. 1997, 38, 3193-3194.
49. A portion of this work has been communicated. (a) Reference 2c. (b) Evans, D. A.; Barnes, D. M. Tetrahedron Lett. 1997, 38, 57-58. (c) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786-787. (d) Evans, D. A.; Shaughnessy, E. A.; Barnes, D. M. Tetrahedron Lett. 1997, 38, 3193-3194.
50. A portion of this work has been communicated. (a) Reference 2c. (b) Evans, D. A.; Barnes, D. M. Tetrahedron Lett. 1997, 38, 57-58. (c) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786-787. (d) Evans, D. A.; Shaughnessy, E. A.; Barnes, D. M. Tetrahedron Lett. 1997, 38, 3193-3194.
51. (a) Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223-2224 and references therein.
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53. For the application of these complexes to the catalysis of the aldol reaction, see ref 3.
54. For the synthesis of (S,S)-tert-butyl bis(oxazoline) (10), see Evans, D. A.; Peterson, G. S.; Johnson, J. S.; Barnes, D. M.; Campos, K. R.; Woerpel, K. A. J. Org. Chem. 1998, 63, 4541-4544.
55. 2 has been solved. See ref 2d.
56. 4 > OTf.
57. The corresponding reactions with cyclopentadiene required 10 h (catalyst 1a) and <4 h (catalyst 1b) at -78 °C. Reference 2c.
58. Grummitt, O.; Becker, E. I. Organic Syntheses, Collective Volume IV; Rabjohn, N., Ed.; Wiley: New York, 1963; pp 771-775.
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61. The imide was insoluble at -20 °C at higher concentrations.
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65. Evans, D. A.; Ellman, J. A.; Britton, T. C. Tetrahedron Lett. 1987, 28, 6141-6144.
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69. Reference 23. Attempts to form the diene through the rearrangement of 2-methylbut-3-yn-2-ol with Ag(I) and acetic anhydride resulted in the formation of a mixture of products which were difficult to separate. See: (a) Banks, R. E.; Miller, J. A.; Nunn, M. J.; Stanley, P.; Weakley, T. J.; Ullah, Z. J. Chem. Soc., Perkin Trans. 1 1981, 1096-1102. (b) Snider, B. B.; Amin S. G. Synth. Commun. 1978, 8, 117.
70. Reference 23. Attempts to form the diene through the rearrangement of 2-methylbut-3-yn-2-ol with Ag(I) and acetic anhydride resulted in the formation of a mixture of products which were difficult to separate. See: (a) Banks, R. E.; Miller, J. A.; Nunn, M. J.; Stanley, P.; Weakley, T. J.; Ullah, Z. J. Chem. Soc., Perkin Trans. 1 1981, 1096-1102. (b) Snider, B. B.; Amin S. G. Synth. Commun. 1978, 8, 117.
71. Reactions carried out at 0 °C were not as clean, while reactions at temperatures lower than -20 °C did not exhibit improved diastereoselectivity.
72. Stoss has provided the precedent for this transformation in the cyclization of the isomeric allylic alcohol: Stoss, P.; Merrath, P. Synlett 1991, 553-554.
73. (a) Petrzilka, T.; Haefliger, W.; Sikemeier, C. Helv. Chim. Acta 1969, 1102.
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91. 1-Phenylbutadiene: thermal = 82:18 endo/exo; catalyzed = 85:15 endo/exo. 1-Phenylthiobutadiene: thermal = 65:35 endo/exo; catalyzed = 98:2 endo/exo. 1-Benzyloxycarbonylaminobutadiene: thermal = 49:51 endo/exo; catalyzed = 72:28 endo/exo.
92. It was not possible to accurately assay the enantioselectivity of the trans product of 1-phenylbutadiene reactions, due to epimerization during the thiolate cleavage reaction.
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106. 2, rt, 1.5 h (86%);
107. 2ZrH(Cl), toluene, rt, 12 h;
108. 3SnCl;
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