Diene hydroacylation from the alcohol or aldehyde oxidation level via ruthenium-catalyzed C-C bond-forming transfer hydrogenation: Synthesis of β,γ-unsaturated ketones

Journal of the American Chemical Society

Volumn 130, Issue 43, 2008, Pages 14120-14122

  Shibahara, Fumitoshi ^a   Bower, John F ^a   Krische, Michael J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; BUTADIENE; CHEMICAL OXYGEN DEMAND; HYDROGENATION; KETONES; ORGANIC POLYMERS; OXIDATION; RUTHENIUM;

ACYCLIC DIENES; ALIPHATIC ALCOHOLS; BENZYLIC; HOMOALLYL ALCOHOLS; HOMOALLYLIC ALCOHOLS; HYDROACYLATION; HYDROGENATIVE COUPLINGS; IDENTICAL CONDITIONS; ISOLATED YIELDS; MYRCENE; OXIDATION LEVELS; RUTHENIUM CATALYSTS; SYNTHESIS OF; TRANSFER HYDROGENATIONS; UNSATURATED KETONES;

ORGANIC COMPOUNDS;

1,3 BUTADIENE; ALDEHYDE; ALKADIENE; ALKANOL; ALLYL ALCOHOL; BENZYL ALCOHOL; CARBONYL DERIVATIVE; ISOPRENE; KETONE DERIVATIVE; MYRCENE; RUTHENIUM;

ACYLATION; ALCOHOL OXIDATION; ARTICLE; CATALYSIS; HYDROGENATION; ISOMERIZATION; METAL BINDING; OXIDATION KINETICS; SYNTHESIS;

ALCOHOLS; ALDEHYDES; ALKADIENES; CATALYSIS; HYDROGENATION; KETONES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; RUTHENIUM; STEREOISOMERISM;

EID: 54849406161     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja805356j     Document Type: Article

References (32)

1. For selected reviews of hydrogenative C-C coupling, see: (a) Ngai, M.-Y.; Kong, J.-R.; Krische, M. J. J. Org. Chem. 2007, 72, 1063.
2. (b) Iida, H.; Krische, M. J. Top. Curr. Chem. 2007, 279, 77.
3. (c) Skucas, E.; Ngai, M.-Y.; Komanduri, V.; Krische, M. J. Acc. Chem. Res. 2007, 40, 1394.
4. For recent examples, see the following. C=X vinylation: (a) Kong, J.-R.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 718.
5. (b) Skucas, E.; Kong, J.-R.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 7242.
6. (c) Barchuk, A.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 8432.
7. (d) Barchuk, A.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 12644.
8. Aldol and Mannich addition: (e) Jung, C.-K.; Garner, S. A.; Krische, M. J. Org. Lett. 2006, 8, 519.
9. (f) Jung, C.-K.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 17051.
10. (g) Bee, C.; Han, S. B.; Hassan, A.; Iida, H.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 2747. C=O allylation:
11. (h) Skucas, E.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 12678.
12. For indium-catalyzed transfer hydrogenative C-C couplings, see: (a) Bower, J. F.; Skucas, E.; Patman, R. L.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 15134.
13. (b) Bower, J. F.; Patman, R. L.; Krische, M. J. Org. Lett. 2008, 10, 1033.
14. (c) Kim, I. S.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 6340.
15. For ruthenium-catalyzed transfer hydrogenative C-C couplings, see: (a) Shibahara, F.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 6338.
16. (b) Patman, R. L.; Williams, V. M.; Bower, J. F.; Krische, M. J. Angew. Chem., Int. Ed. 2008, 47, 5220.
17. (c) Ngai, M.-Y.; Skucas, E.; Krische, M. J. Org. Lett. 2008, 10, 2705.
18. Alcohols participate in formal substitution under the conditions of hydrogen autotransfer to furnish products of C-C bond formation. These processes employ preformed nucleophiles that olefinate the transient carbonyl, which is then reduced to the saturated adduct. In contrast, the processes developed in our laboratory employ unsaturates as pronucleophiles and deliver products of carbonyl addition. For reviews of hydrogen autotransfer, see: (a) Guillena, G.; Ramón, D. J.; Yus, M. Angew. Chem., Int. Ed. 2007, 46, 2358.
19. (b) Hamid, M. H. S. A.; Slatford, P. A.; Williams, J. M. J. Adv. Synth. Catal. 2007, 349, 1555.
20. For intermolecular ruthenium-catalyzed hydroacylation, see: (a) Isnard, P.; Denise, B.; Sneeden, R. P. A.; Cognion, J. M.; Durual, P. J. Organomet. Chem. 1982, 240, 285.
21. (b) Isnard, P.; Denise, B.; Sneeden, R. P. A.; Cognion, J. M.; Durual, P. J. Organomet. Chem. 1983, 256, 135.
22. (c) Kondo, T.; Tsuji, Y.; Watanabe, Y. Tetrahedron Lett. 1987, 28, 6229.
23. (d) Kondo, T.; Akazome, M.; Tsuji, Y.; Watanabe, Y. J. Org. Chem. 1990, 55, 1286.
24. (e) Kondo, T.; Hiraishi, N.; Morisaki, Y.; Wada, K.; Watanabe, Y.; Mitsudo, T.-A. Organometallics 1998, 17, 2131.
25. Concurrent with submission of our work, an aligned study was disclosed by Ryu: Omura, S.; Fukuyama, T.; Horiguchi, J.; Murakami, Y.; Ryu, I. J. Am. Chem. Soc. 2008, 130. in press (http://dx.doi.org/10.1021/ ja806929y).
26. Dobson, A.; Robinson, S. R.; Uttley, M. F. J. Chem. Soc., Dalton Trans. 1974, 370.
27. For reviews on enantioselective carbonyl allylation, see: (a) Ramachandran, P. V. Aldrichimica Acta 2002, 35, 23.
28. (b) Kennedy, J. W. J.; Hall, D. G. Angew. Chem., Int. Ed. 2003, 42, 4732.
29. (c) Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103. 2763.
30. (d) Yu, C.-M.; Youn, J.; Jung, H.-K. Bull. Korean Chem. Soc. 2006, 27, 463.
31. (e) Marek, I.; Sklute, G. Chem. Commun. 2007, 1683.
32. (f) Hall, D. G. Synlett 2007, 1644.