Catalytic asymmetric carbon-carbon bond formation using alkenes as alkylmetal equivalents

Nature Chemistry

Volumn 4, Issue 8, 2012, Pages 649-654

  Maksymowicz, Rebecca M ^a   Roth, Philippe M C ^a   Fletcher, Stephen P ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84864343287     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.1394     Document Type: Article

References (49)

1. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis (Pergamon, 1992).
2. Hayashi, T. & Yamasaki, K. Rhodium-catalyzed asymmetric 1,4-Addition and its related asymmetric reactions. Chem. Rev. 103, 2829-2844 (2003).
3. Krause, N. & Hoffmann-Röder, A. Recent advances in catalytic enantioselective Michael additions. Synthesis 171-196 (2001). (Pubitemid 32150754)
4. Thaler, T. & Knochel, P. Copper-catalyzed asymmetric Michael addition of magnesium, zinc, and aluminum organometallic reagents: Efficient synthesis of chiral molecules. Angew. Chem. Int. Ed. 48, 645-648 (2009).
5. Jerphagnon, T., Pizzuti, M. G., Minnaard, A. J. & Feringa, B. L. Recent advances in enantioselective copper-catalyzed 1,4-Addition. Chem. Soc. Rev. 38, 1039-1075 (2009).
6. Harutyunyan, S. R., den Hartog, T., Geurts, K., Minnaard, A. J. & Feringa, B. L. Catalytic asymmetric conjugate addition and allylic alkylation with Grignard reagents. Chem. Rev. 108, 2824-2852 (2008).
7. Alexakis, A., Bäckvall, J. E., Krause, N., Pàmies, O. & Diéguez, M. Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions. Chem. Rev. 108, 2796-2823 (2008).
8. Feringa, B. L., Badorrey, R., Peña, D., Harutyunyan, S. R. & Minnaard, A. J. Copper-catalyzed asymmetric conjugate addition of Grignard reagents to cyclic enones. Proc. Natl Acad. Sci. USA 101, 5834-5838 (2004). (Pubitemid 38520488)
9. Martin, D. et al. Copper-catalyzed asymmetric conjugate addition of Grignard reagents to trisubstituted enones. Construction of all-carbon quaternary chiral centers. J. Am. Chem. Soc. 128, 8416-8417 (2006).
10. Wang, S. Y., Ji, S. J. & Loh, T. P. Cu(I) Tol-BINAP-catalyzed enantioselective Michael reactions of Grignard reagents and unsaturated esters. J. Am. Chem. Soc. 129, 276-277 (2007).
11. Robert, T., Velder, J. & Schmalz, H. G. Enantioselective Cu-catalyzed 1,4- Addition of Grignard reagents to cyclohexenone using Taddol-derived phosphine-phosphite ligands and 2-methyl-THF as a solvent. Angew. Chem. Int. Ed. 47, 7718-7721 (2008).
12. Feringa, B. L., Pineschi, M., Arnold, L. A., Imbos, R. & de Vries, A. H. M. Highly enantioselective catalytic conjugate addition and tandem conjugate addition- Aldol reactions of organozinc reagents. Angew. Chem. Int. Ed. 36, 2620-2623 (1997).
13. Degrado, S. J., Mizutani, H. & Hoveyda, A. H. Modular peptide-based phosphine ligands in asymmetric catalysis: Efficient and enantioselective Cu-catalyzed conjugate additions to five-, six-, and seven-membered cyclic enones. J. Am. Chem. Soc. 123, 755-756 (2001). (Pubitemid 32106024)
14. Alexakis, A., Benhaim, C., Rosset, S. & Humam, M. Dramatic improvement of the enantiomeric excess in the asymmetric conjugate addition reaction using new experimental conditions. J. Am. Chem. Soc. 124, 5262-5263 (2002). (Pubitemid 34506911)
15. Fraser, P. K. & Woodward, S. Highly enantioselective conjugate addition of AlMe3 to linear aliphatic enones by a designed catalyst. Chem. Eur. J. 9, 776-783 (2003).
16. d'Augustin, M., Palais, L. & Alexakis, A. Enantioselective copper-catalyzed conjugate addition to trisubstituted cyclohexenones: Construction of stereogenic quaternary centers. Angew. Chem. Int. Ed. 44, 1376-1378 (2005). (Pubitemid 40343553)
17. May, T. L., Brown, M. K. & Hoveyda, A. H. Enantioselective synthesis of allcarbon quaternary stereogenic centers by catalytic asymmetric conjugate additions of alkyl and aryl aluminum reagents to five-, six-, and sevenmembered- ring beta-substituted cyclic enones. Angew. Chem. Int. Ed. 47, 7358-7362 (2008).
18. Perez, M. et al. Catalytic asymmetric carbon-carbon bond formation via allylic alkylations with organolithium compounds. Nature Chem. 3, 377-381 (2011).
19. Young, I. S. & Baran, P. S. Protecting-group-free synthesis as an opportunity for invention. Nature Chem. 1, 193-205 (2009).
20. Knochel, P. et al. Highly functionalized organomagnesium reagents prepared through halogen-metal exchange. Angew. Chem. Int. Ed. 42, 4302-4320 (2003). (Pubitemid 37221310)
21. Howell, G. P. Asymmetric and diastereoselective conjugate addition reactions: C-C bond formation at large scale. Org. Process Res. Dev. doi:10.1021/op200381w (2012).
22. Anastas, P. T. & Warner, J. C. Green Chemistry: Theory and Practice (Oxford Univ. Press, 1998).
23. Rieke, R. D. Preparation of organometallic compounds from highly reactive metal powders. Science 246, 1260-1264 (1989).
24. Blümke, T., Chen, Y. H., Peng, Z. & Knochel, P. Preparation of functionalized organoaluminiums by direct insertion of aluminium to unsaturated halides. Nature Chem. 2, 313-318 (2010).
25. Shirakawa, E., Ikeda, D., Masui, S., Yoshida, M. & Hayashi, T. Iron-copper cooperative catalysis in the reactions of alkyl Grignard reagents: Exchange reaction with alkenes and carbometalation of alkynes. J. Am. Chem. Soc. 134, 272-279 (2012).
26. Bower, J. F. & Krische, M. J. in Handbook of Green Chemistry Vol. 1 (eds Anastas, P. T. & Crabfree, R. H.) Ch. 8 (Wiley-VCH, 2009).
27. Ohmiya, H., Yoshida, M. & Sawamura, M. Copper-catalyzed conjugate additions of alkylboranes to imidazolyl a,b-unsaturated ketones: Formal reductive conjugate addition of terminal alkenes. Org. Lett. 13, 482-485 (2010).
28. Wipf, P. & Xu, W. J. Preparation of allylic alcohols by alkene transfer from zirconium to zinc. Tetrahedron Lett. 35, 5197-5200 (1994). (Pubitemid 24227809)
29. Alexakis, A. et al. Highly enantioselective copper(I)-phosphoramidite- catalysed additions of organoaluminium reagents to enones. Chem. Commun. 2843-2845 (2005). (Pubitemid 40904173)
30. Akiyama, K., Gao, F. & Hoveyda, A. H. Stereoisomerically pure trisubstituted vinylaluminum reagents and their utility in copper-catalyzed enantioselective synthesis of 1,4-dienes containing Z or E alkenes. Angew. Chem. Int. Ed. 49, 419-423 (2010).
31. Miller, K. M., Huang, W. S. & Jamison, T. F. Catalytic asymmetric reductive coupling of alkynes and aldehydes: Enantioselective synthesis of allylic alcohols and alpha-hydroxy ketones. J. Am. Chem. Soc. 125, 3442-3443 (2003). (Pubitemid 36512413)
32. Bower, J. F., Kim, I. S., Patman, R. L. & Krische, M. J. Catalytic carbonyl addition through transfer hydrogenation: A departure from preformed organometallic reagents. Angew. Chem. Int. Ed. 48, 34-46 (2009).
33. Chauvin, Y., Schrock, R. R. & Grubbs, R. H. Nobel lectures. Angew. Chem. Int. Ed. 45, 3740-3765 (2006).
34. Beletskaya, I. P. & Cheprakov, A. V. The Heck reaction as a sharpening stone of palladium catalysis. Chem. Rev. 100, 3009-3066 (2000).
35. Knowles, W. S., Noyori, R. & Sharpless, K. B. Nobel lectures. Angew. Chem. Int. Ed. 41, 1998-2032 (2002).
36. Buchwald, S. L., LaMaire, S. J. & Nielsen, R. B. Schwartz reagent. Org. Synth. 71, 77-82 (1993).
37. Schwartz, J. & Labinger, J. A. Hydrozirconation: New transition-metal reagent for organic-synthesis. Angew. Chem. Int. Ed. 15, 333-340 (1976).
38. Carr, D. B. & Schwartz, J. Preparation of organoaluminum compounds by hydrozirconation-transmetalation. J. Am. Chem. Soc. 101, 3521-3531 (1979).
39. Negishi, E. I. Magical power of transition metals: Past, present, and future (Nobel lecture). Angew. Chem. Int. Ed. 50, 6738-6764 (2011).
40. Lipshutz, B. H. & Ellsworth, E. L. Hydrozirconation-transmetalation-A mild, direct route to higher-order vinylic cuprates from monosubstituted acetylenes. J. Am. Chem. Soc. 112, 7440-7441 (1990).
41. Corey, E. J. & Carpino, P. A simplified synthesis of (+)-brefeldin-A. Tetrahedron Lett. 31, 7555-7558 (1990).
42. Wipf, P. & Smitrovich, J. H. Transmetalation reactions of alkylzirconocenes- copper-catalyzed conjugate addition to enones. J. Org. Chem. 56, 6494-6496 (1991).
43. Venanzi, L. M., Lehmann, R., Keil, R. & Lipshutz, B. H. Copper-catalyzed allylic alkylations of alkylzirconium intermediates. Tetrahedron Lett. 33, 5857-5860 (1992).
44. Wipf, P., Xu, W. J., Smitrovich, J. H., Lehmann, R. & Venanzi, L. M. Coppercatalyzed conjugate additions of organozirconocenes. Synthetic and mechanistic studies. Tetrahedron 50, 1935-1954 (1994). (Pubitemid 24098878)
45. Wipf, P. & Jahn, H. Synthetic applications of organochlorozirconocene complexes. Tetrahedron 52, 12853-12910 (1996). (Pubitemid 26316613)
46. Teichert, J. F. & Feringa, B. L. Phosphoramidites: Privileged ligands in asymmetric catalysis. Angew. Chem. Int. Ed. 49, 2486-2528 (2010).
47. Brown, M. K., Degrado, S. J. & Hoveyda, A. H. Highly enantioselective Cucatalyzed conjugate additions of dialkylzinc reagents to unsaturated furanones and pyranones: Preparation of air-stable and catalytically active Cu-peptide complexes. Angew. Chem. Int. Ed. 44, 5306-5310 (2005). (Pubitemid 41223891)
48. Bilčik, F., Drusan, M., Marák, J. & Šebesta, R. Enantioselective one-pot conjugate addition of Grignard reagents to cyclic enones followed by amidomethylation. J. Org. Chem. 77, 760-765 (2012).
49. Naeemi, Q., Robert, T., Kranz, D. P., Velder, J. & Schmalz, H. G. Chiral phosphine-phosphite ligands in the enantioselective 1,4-Addition of Grignard reagents to a,b-unsaturated carbonyl compounds. Tetrahedron Asymm. 22, 887-892 (2011).