Catalytic carbonyl Z-dienylation via multicomponent reductive coupling of acetylene to aldehydes and α-ketoesters mediated by hydrogen: Carbonyl insertion into cationic rhodacyclopentadienes

Journal of the American Chemical Society

Volumn 128, Issue 50, 2006, Pages 16040-16041

  Kong, Jong Rock ^a   Krische, Michael J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ALDEHYDE; ALPHA KETOESTER DERIVATIVE; CARBONYL DERIVATIVE; HYDROGEN;

ARTICLE; CATALYSIS; ENANTIOSELECTIVITY; HYDROGENOLYSIS; OXIDATION; REACTION ANALYSIS;

ACETYLENE; ALDEHYDES; CATALYSIS; CATIONS; CYCLOPENTANES; HYDROGEN; KETONES; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 33845585619     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0664786     Document Type: Article

References (42)

1. For recent reviews on alkene hydroformylation, see: (a) Eilbracht, P.; Barfacker, L.; Buss, C.; Hollmann, C.; Kitsos-Rzychon, B. E.; Kranemann, C. L.; Rische, T.; Roggenbuck, R.; Schmidt, A. Chem. Rev. 1999, 99, 3329.
2. (b) Nozaki, K. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 1, p 381.
3. (c) Breit, B. Acc. Chem. Res. 2003, 36, 264.
4. For recent examples of hydrogen-mediated C-C couplings developed in our laboratory, see: (a) Jang, H.-Y.; Hughes, F. W.; Gong, H.; Zhang, J.; Brodbelt, J. S.; Krische, M. J. Am. Chem. Soc. 2005, 127, 6174.
5. (b) Kong, J. R.; Cho, C.-W.; Krische, M. J. J. Am. Chem. Soc. 2005, 127, 11269.
6. (c) Jung, C.-K.; Garner, S. A.; Krische, M. J. Org. Lett. 2006, 8, 519.
7. (d) Kong, J. R.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 718.
8. (e) Cho, C.-W.; Krische, M. J. Org. Lett. 2006, 8, 3873.
9. (f) Rhee, J. U.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 10674.
10. Prior to our work, the following hydrogen-mediated C-C bond formations not involving CO coupling were reported: (a) Molander, G. A.; Hoberg, J. O. J. Am. Chem. Soc. 1992, 114, 3123.
11. (b) Kokubo, K.; Miura, M.; Nomura, M. Organometallics 1995, 14, 4521.
12. Kirk-Othmer's Encyclopedia of Chemical Technology, 5th ed.; Wiley: Hoboken, NJ, 2004; Vol. 1, pp 216-217.
13. For recent reviews encompassing metal-catalyzed multicomponent coupling, see: (a) Ikeda, S.-I. Angew. Chem., Int. Ed. 2003, 42, 5120.
14. (b) Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890.
15. (c) Multicomponent Reactions; Zhu, J., Bienaymé. H., Eds.; Wiley-VCH: Weinheim, Germany, 2005.
16. (d) Ramón, D. J.; Yus, M. Angew. Chem., Int. Ed. 2005, 44, 1602.
17. 2ZrHCl followed by transmetalation to furnish organozinc reagents, which participate in catalytic asymmetric additions: (a) Oppolzer, W.; Radinov, R. Helv. Chim. Acta 1992, 75, 170.
18. (b) Oppolzer, W.; Radinov, R. J. Am. Chem. Soc. 1993, 115, 1593.
19. (c) Soai, K.; Takahashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1257.
20. (d) Wipf, P.; Xu, W. Tetrahedron Lett. 1994, 35, 5197.
21. (e) Wipf, P.; Xu, W. Org. Synth. 1996, 74, 205.
22. (f) Wipf, P.; Ribe, S. J. Org. Chem. 1998, 63, 6454.
23. (g) Oppolzer, W.; Radinov, R. N.; El-Sayed, E. J. Org. Chem. 2001, 66, 4766.
24. (h) Dahmen, S.; Bräse, S. Org. Lett. 2001, 3, 4119.
25. (i) Ji, J.-X.; Qiu, L.-Q.; Yip, C. W.; Chan, A. S. C. J. Org. Chem. 2003, 68, 1589.
26. (j) Lurain, A. E.; Walsh, P. J. J. Am. Chem. Soc. 2003, 125, 10677.
27. (k) Ko, D.-H.; Kang, S.-W.; Kim, K. H.; Chung, Y.; Ha, D.-C. Bull. Korean Chem. Soc. 2004, 25, 35.
28. (l) Jeon, S.-J.; Chen, Y. K.; Walsh, P. J. Org. Lett. 2005, 7, 1729.
29. (m) Li, H.; Walsh, P. J. J. Am. Chem. Soc. 2005, 127, 8355.
30. (n) Jeon, S.-J.; Fisher, E. L.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2006, 128, 9618.
31. The direct metal-catalyzed intermolecular reductive coupling of substituted alkynes to carbonyl compounds has been achieved under the conditions of Ni catalysis (see ref 5b) and Rh catalysis (see refs 2d-f).
32. Cui, X.; Burgess, K. Chem. Rev. 2005, 105, 3272 and references cited therein.
33. For a discussion on mass-transter-limitation effects in catalysis, see: Roberts, G. W. In Catalysis in Organic Syntheses: Rylander, P. N., Greenfield, H., Eds.; Academic Press: New York, 1976; pp 1-48.
34. Bianchini, C.; Caulton, K. G.; Chardon, C.; Eisenstein, O.; Folting, K.; Johnson, T. J.; Meli, A.; Peruzzini, M.; Rauscher, D. J.; Streib, W. E.; Vizza, F. J. Am. Chem. Soc. 1991, 113, 5127 and references cited therein.
35. For examples of carbonyl insertion into a Rh-C bond followed by protonolytic cleavage or β-hydride elimination of the resulting rhodium alkoxide, see: (a) Krug, C.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 1674.
36. (b) Fujii, T.; Koike, T.; Mori, A.; Osakada, K. Synlett 2002, 298.
37. Hutschka, F.; Dedieu, A.; Leitner, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 1742.
38. (a) Müller, E.; Thomas, R.; Zountsas, G. Liebigs Ann. Chem. 1972, 16.
39. (b) Müller, E.; Winter, W. Chem. Ber. 1972, 105, 2523.
40. (c) Müller, E.; Winter, W. Liebigs Ann. Chem. 1975, 41.
41. (d) Scheller, A.; Winter, W.; Müller, E. Liebigs Ann. Chem. 1976, 1448.
42. For hydrogen-mediated reductive cyclization of 1,6-diynes, see: Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 7875.