Enantioselective synthesis of α-alkyl-β,γ-unsaturated esters through efficient Cu-catalyzed allylic alkylations

Journal of the American Chemical Society

Volumn 125, Issue 16, 2003, Pages 4690-4691

  Murphy, Kerry E ^a   Hoveyda, Amir H ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; COPPER; ESTER DERIVATIVE;

ADDITION REACTION; ALKYLATION; ARTICLE; CATALYSIS; DIMERIZATION; ENANTIOSELECTIVITY; HYDROGENATION; REACTION ANALYSIS; SYNTHESIS;

ALKYLATION; ALLYL COMPOUNDS; COPPER; ESTERS; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; ZINC;

EID: 0037462119     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0300618     Document Type: Article

References (30)

1. For recent examples, see: (a) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415.
2. (b) Ahman, J.; Wolfe, J. P.; Troutman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918-1919.
3. (c) Trost, B. M.; Schroeder, G. M. J. Am. Chem. Soc. 1999, 121, 6759-6760.
4. (d) Nakoji, M.; Kanayama, T.; Okino, T.; Takemoto, Y. Org. Lett. 2001, 3, 3329-3331.
5. (a) Ibuka, T.; Habashita, H.; Funakoshi, S.; Fujii, N.; Oguschi, Y.; Uyehara, T.; Yamamoto, Y. Angew. Chem., Int. Ed. Engl. 1990, 29, 801-803. (b) Venanzi, L. M.; Lehmann, R.; Keil, R.; Lipschutz, B. H. Tetrahedron Lett. 1992, 33, 5857-5860. (c) Oishi, S.; Kamano, T.; Niida, A.; Odagaki, Y.; Tamamura, H.; Otaka, A.; Hamanaka, N.; Fujii, N. Org. Lett. 2002, 4, 1051-1054. For a related enantioselective process see: (d) Luchaco-Cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193.
6. (a) Ibuka, T.; Habashita, H.; Funakoshi, S.; Fujii, N.; Oguschi, Y.; Uyehara, T.; Yamamoto, Y. Angew. Chem., Int. Ed. Engl. 1990, 29, 801-803. (b) Venanzi, L. M.; Lehmann, R.; Keil, R.; Lipschutz, B. H. Tetrahedron Lett. 1992, 33, 5857-5860. (c) Oishi, S.; Kamano, T.; Niida, A.; Odagaki, Y.; Tamamura, H.; Otaka, A.; Hamanaka, N.; Fujii, N. Org. Lett. 2002, 4, 1051-1054. For a related enantioselective process see: (d) Luchaco-Cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193.
7. (a) Ibuka, T.; Habashita, H.; Funakoshi, S.; Fujii, N.; Oguschi, Y.; Uyehara, T.; Yamamoto, Y. Angew. Chem., Int. Ed. Engl. 1990, 29, 801-803. (b) Venanzi, L. M.; Lehmann, R.; Keil, R.; Lipschutz, B. H. Tetrahedron Lett. 1992, 33, 5857-5860. (c) Oishi, S.; Kamano, T.; Niida, A.; Odagaki, Y.; Tamamura, H.; Otaka, A.; Hamanaka, N.; Fujii, N. Org. Lett. 2002, 4, 1051-1054. For a related enantioselective process see: (d) Luchaco-Cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193.
8. (a) Ibuka, T.; Habashita, H.; Funakoshi, S.; Fujii, N.; Oguschi, Y.; Uyehara, T.; Yamamoto, Y. Angew. Chem., Int. Ed. Engl. 1990, 29, 801-803. (b) Venanzi, L. M.; Lehmann, R.; Keil, R.; Lipschutz, B. H. Tetrahedron Lett. 1992, 33, 5857-5860. (c) Oishi, S.; Kamano, T.; Niida, A.; Odagaki, Y.; Tamamura, H.; Otaka, A.; Hamanaka, N.; Fujii, N. Org. Lett. 2002, 4, 1051-1054. For a related enantioselective process see: (d) Luchaco-Cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193.
9. For catalytic asymmetric allylic substitutions with alkylzincs, see: (a) Dubner, F.; Knochel, P. Tetrahedron Lett. 2000, 41, 9233-9237. (b) Luchaco-Cullis, C. A.; Mizutani, H.; Murphy, K. E.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2001, 40, 1456-1460. (c) Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169-1171. (d) Ongeri, S.; Piarulli, U.; Roux, M.; Monti, C.; Gennari, C. Helv. Chim. Acta 2002, 85, 3388-3399. (e) Piarulli, U.; Daubos, P.; Claverie, C.; Roux, M.; Gennari, C. Angew. Chem., Int. Ed. 2003, 42, 234-236.
10. For catalytic asymmetric allylic substitutions with alkylzincs, see: (a) Dubner, F.; Knochel, P. Tetrahedron Lett. 2000, 41, 9233-9237. (b) Luchaco-Cullis, C. A.; Mizutani, H.; Murphy, K. E.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2001, 40, 1456-1460. (c) Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169-1171. (d) Ongeri, S.; Piarulli, U.; Roux, M.; Monti, C.; Gennari, C. Helv. Chim. Acta 2002, 85, 3388-3399. (e) Piarulli, U.; Daubos, P.; Claverie, C.; Roux, M.; Gennari, C. Angew. Chem., Int. Ed. 2003, 42, 234-236.
11. For catalytic asymmetric allylic substitutions with alkylzincs, see: (a) Dubner, F.; Knochel, P. Tetrahedron Lett. 2000, 41, 9233-9237. (b) Luchaco-Cullis, C. A.; Mizutani, H.; Murphy, K. E.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2001, 40, 1456-1460. (c) Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169-1171. (d) Ongeri, S.; Piarulli, U.; Roux, M.; Monti, C.; Gennari, C. Helv. Chim. Acta 2002, 85, 3388-3399. (e) Piarulli, U.; Daubos, P.; Claverie, C.; Roux, M.; Gennari, C. Angew. Chem., Int. Ed. 2003, 42, 234-236.
12. For catalytic asymmetric allylic substitutions with alkylzincs, see: (a) Dubner, F.; Knochel, P. Tetrahedron Lett. 2000, 41, 9233-9237. (b) Luchaco-Cullis, C. A.; Mizutani, H.; Murphy, K. E.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2001, 40, 1456-1460. (c) Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169-1171. (d) Ongeri, S.; Piarulli, U.; Roux, M.; Monti, C.; Gennari, C. Helv. Chim. Acta 2002, 85, 3388-3399. (e) Piarulli, U.; Daubos, P.; Claverie, C.; Roux, M.; Gennari, C. Angew. Chem., Int. Ed. 2003, 42, 234-236.
13. For catalytic asymmetric allylic substitutions with alkylzincs, see: (a) Dubner, F.; Knochel, P. Tetrahedron Lett. 2000, 41, 9233-9237. (b) Luchaco-Cullis, C. A.; Mizutani, H.; Murphy, K. E.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2001, 40, 1456-1460. (c) Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169-1171. (d) Ongeri, S.; Piarulli, U.; Roux, M.; Monti, C.; Gennari, C. Helv. Chim. Acta 2002, 85, 3388-3399. (e) Piarulli, U.; Daubos, P.; Claverie, C.; Roux, M.; Gennari, C. Angew. Chem., Int. Ed. 2003, 42, 234-236.
14. Isolation: (a) Juagdan, E. G.; Kalidindi, R. S.; Scheuer, P. J.; Kelly-Borges, M. Tetrahedron Lett. 1995, 36. 2905-2908.
15. (b) Takanashi, S.; Takagi, M.; Takakawa, H.; Mori, K. J. Chem. Soc., Perkin Trans. 1 1998, 1603-1606.
16. (c) Hoye, R. C.; Baigorria, A. S.; Danielson, M. E.: Pragman, A. A.; Rajapakse, H. A. J. Org. Chem. 1999, 64, 2450-2453.
17. Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668-1671. See the Supporting Information for details of screening studies.
18. (a) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756.
19. (b) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779-781.
20. (c) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 13362-13363.
21. (d) Hird, A. W.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 2003, 42, 1276-1279.
22. Isolated yields are at times moderate due to product volatility.
23. 2Zn) result in efficient alkylations that proceed with low enantioselectivity (<20% ee).
24. Louie, J.; Bielawski, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 11312-11313.
25. Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179.
26. Van Horn, D. E.; Negishi, E. J. Am. Chem. Soc. 1978, 100, 2252-2254.
27. Higher catalyst loading is required probably due to internal chelation of the terminal Ru carbene with the neighboring carbonyl oxygen, which diminishes its reactivity. Metathesis yields suffer from formation of homodimers of 2h. For utility of 12 in cross-metathesis, see: (a) Cossy, J.; BouzBouz, S.; Hoveyda, A. H. J. Organomet. Chem. 2001, 624, 327-332. (b) Randl, S.; Gessler, S.; Wakamatsu, H.; Blechert, S. Synlett 2001, 430-432.
28. Higher catalyst loading is required probably due to internal chelation of the terminal Ru carbene with the neighboring carbonyl oxygen, which diminishes its reactivity. Metathesis yields suffer from formation of homodimers of 2h. For utility of 12 in cross-metathesis, see: (a) Cossy, J.; BouzBouz, S.; Hoveyda, A. H. J. Organomet. Chem. 2001, 624, 327-332. (b) Randl, S.; Gessler, S.; Wakamatsu, H.; Blechert, S. Synlett 2001, 430-432.
29. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
30. Felix, A. M. J. Org. Chem. 1974, 39, 1427-1429.