Carbometallation Reactions

Copper-Catalyzed Asymmetric Synthesis

Volumn 9783527332045, Issue , 2014, Pages 267-282

  Didier, Dorian ^a   Marek, Ilan ^a  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

Carbometallation; Diastereoselectivity; Enantioselectivity; Functionalization; Homologation; Regioselectivity

Indexed keywords

ENANTIOSELECTIVITY;

CARBOMETALLATION; DIASTEREOSELECTIVITIES; FUNCTIONALIZATIONS; HOMOLOGATION;

REGIOSELECTIVITY;

EID: 84926429651     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527664573.ch10     Document Type: Chapter

References (45)

1. Grignard, V. (1900) Compt. Rend., 130, 1322.
2. Ziegler, K. and Bähr, K. (1928) Chem. Ber., 61, 253.
3. Normant, J.F. and Alexakis, A. (1981) Synthesis, 1981, 841;
4. Nakamura, E. (1996) Pure Appl. Chem., 68, 123;
5. Fallis, A.G. and Forgione, P. (2001) Tetrahedron, 57, 5899;
6. Basheer, A. and Marek, I. (2010) Beilstein J. Org. Chem., 6 (77);
7. Itami, K. and Yoshida, J.I. (2008) Carbomagnesiation reactions, in The Chemistry of Organomagnesium Compounds (eds Z. Rappoport and I. Marek), John Wiley & Sons, Ltd, Chichester;
8. Chemla, F. and Ferreira, F. (2011) Carbocupration of alkynes, in The Chemistry of Organocopper Compounds (eds Z. Rappoport and I. Marek), John Wiley & Sons, Ltd, Chichester.
9. Marek, I. (1999) J. Chem. Soc., Perkin Trans. 1, 535.
10. Mori, S. and Nakamura, E. (1999) Tetrahedron Lett., 40, 5019;
11. Mori, S., Hirai, A., Nakamura, M., and Nakamura, E. (2000) Tetrahedron, 56, 2085.
12. Nakamura, E., Miyachi, Y., Koga, N., and Morokuma, K. (1992) J. Am. Chem. Soc., 114, 6686;
13. Nakamura, E., Nakamura, M., Miyachi, Y., Koga, N., and Morokuma, K. (1993) J. Am. Chem. Soc., 115, 99.
14. Mori, S. and Nakamura, E. (1999) J. Mol. Struct. (THEOCHEM), 461, 167.
15. Hartwig, J.F. (2010) Organotransition Metal Chemistry: From Principles to Catalysis, University Science Book, Herndon, VA.
16. Kitaura, K. and Morokuma, K. (1976) Int. J. Quantum Chem., 10, 325;
17. Morokuma, K. (1971) J. Chem. Phys., 55, 1236;
18. Simaan, S., Masarwa, A., and Marek, I. (2007) Angew. Chem. Int. Ed., 46, 7364.
19. Fox, J.M. and Yan, N. (2005) Curr. Org. Chem., 9, 719;
20. Nakamura, M., Isobe, H., and Nakamura, E. (2003) Chem. Rev., 103, 1295.
21. Nakamura, E., Isaka, M., and Matsuzawa, S. (1988) J. Am. Chem. Soc., 110, 1297.
22. Liao, L. and Fox, J.M. (2002) J. Am. Chem. Soc., 124, 14322.
23. Yan, N., Liu, X., and Fox, J.M. (2008) J. Org. Chem., 73, 563.
24. Shirakawa, E., Yamagami, T., Kimura, T., Yamaguchi, S., and Hayashi, T. (2005) J. Am. Chem. Soc., 127, 17164.
25. Simaan, S., Masarwa, A., Bertus, P., and Marek, I. (2006) Angew. Chem. Int. Ed., 45, 3963;
26. Simaan, S., Masarwa, A., Zohar, E., Stanger, A., Bertus, P., and Marek, I. (2009) Chem. Eur. J., 15, 8449.
27. Rubina, M., Rubin, M., and Gevorgyan, V. (2003) J. Am. Chem. Soc., 125, 7198.
28. Nalesnik, T.E., Freudenberg, J.H., and Orchin, M. (1982) J. Organomet. Chem., 236, 95;
29. Matsui, Y. and Orchin, M. (1983) J. Organomet. Chem., 244, 369;
30. Sherrill, W.M. and Rubin, M. (2008) J. Am. Chem. Soc., 130, 13804.
31. Tarwade, V., Liu, X., Yan, N., and Fox, J.M. (2009) J. Am. Chem. Soc., 131, 5382.
32. Alexakis, A., Bäckvall, J.E., Krause, N., Pàmies, O., and Diéguez, M. (2008) Chem. Rev., 108, 2796.
33. Sklute, G., Bolm, C., and Marek, I. (2007) Org. Lett., 9, 1259.
34. Sklute, G., Amsallem, D., Shibli, A., Varghese, J.P., and Marek, I. (2003) J. Am. Chem. Soc., 125, 11776;
35. Sklute, G. and Marek, I. (2006) J. Am. Chem. Soc., 128, 4642.
36. Maezaki, N., Sawamoto, H., Yoshigami, R., Suzuki, T., and Tanaka, T. (2003) Org. Lett., 5, 1345.
37. Das, J.P. and Marek, I. (2011) Chem. Commun., 47, 4593.
38. Rona, P. and Crabbé, P. (1969) J. Am. Chem. Soc., 91, 3289.
39. Alexakis, A., Mangeney, P., and Normant, J.F. (1985) Tetrahedron Lett., 26, 4197;
40. Alexakis, A., Mangeney, P., Normant, J.F., Ghribi, I., Marek, I., Sedrani, R., and Guir, C. (1988) Pure Appl. Chem., 60, 49;
41. Marek, I., Alexakis, A., Mangeney, P., and Normant, J.F. (1992) Bull. Soc. Chim. Fr., 129, 171.
42. Claesson, A. and Olsson, L.I. (1979) Chem. Soc., Chem. Commun., 524;
43. Chenser, J.H.B., Howard, J.A., and Mile, B. (1985) J. Am. Chem. Soc., 107, 4190.
44. Marek, I., Mangeney, P., Alexakis, A., and Normant, J.F. (1989) Tetrahedron Lett., 27, 5499;
45. Alexakis, A., Marek, I., Mangeney, P., and Normant, J.F. (1990) J. Am. Chem. Soc., 112, 8042.