Catalytic hydroacylation as an approach to homoaldol products

Organic Letters

Volumn 13, Issue 23, 2011, Pages 6216-6219

  Murphy, Stephen K ^a   Petrone, David A ^a   Coulter, Matthew M ^a   Dong, Vy M ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

3-HYDROXYBUTANAL; ALCOHOL DERIVATIVE; ALDEHYDE; ALDOL; SALICYLALDEHYDE; STYRENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

ALCOHOLS; ALDEHYDES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; STYRENES;

EID: 82355160895     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202663p     Document Type: Article

References (34)

1. Kuwajima, I.; Nakamura, E. Top. Curr. Chem. 1990, 155, 1
2. Seebach, D. Angew. Chem., Int. Ed. 1979, 18, 239
3. Hoppe, D. Synthesis 2009, 1, 43
4. Crimmins, M. T.; Nantermet, P. G. Org. Prep. Proc. 1993, 25, 43
5. Kuwajima, I.; Nakamura, E. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergammon: Oxford, 1991; p 441. For a comprehensive full paper on the homoaldol reaction, see
6. Lettan, R. B., II; Galliford, C. V.; Woodward, C. C.; Scheidt, K. A. J. Am. Chem. Soc. 2009, 131, 8805
7. Trost, B. M. Science 1991, 254, 1471
8. Willis, M. C. Chem. Rev. 2010, 110, 725
9. Fu, G. C. In Modern Rhodium-Catalyzed Reactions; Evans, P. A., Ed.; Wiley-VCH: New York, 2005; p 79. For selected examples of activated or strained olefins in Rh-catalyzed intermolecular olefin hydroacylation, see
10. Osborne, J. D.; Willis, M. C. Chem. Commun. 2008, 5025
11. Tanaka, K.; Shibata, Y.; Suda, T.; Hagiwara, Y.; Hirano, M. Org. Lett. 2007, 9, 1215
12. Osborne, J. D.; Randell-Sly, H. E.; Currie, G. S.; Cowley, A. R.; Willis, M. C. J. Am. Chem. Soc. 2008, 130, 17232
13. Kokubu, K.; Matsumasa, K.; Nishinaka, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1999, 72, 303
14. Stemmler, R. T.; Bolm, C. Adv. Synth. Catal. 2007, 349, 1185
15. Phan, D. H. T.; Kou, K. G. M.; Dong, V. M. J. Am. Chem. Soc. 2010, 132, 16354
16. Coulter, M. M.; Kou, K. G. M.; Galligan, B.; Dong, V. M. J. Am. Chem. Soc. 2010, 132, 16330
17. Imai, M.; Tanaka, M.; Tanaka, K.; Yamamoto, Y.; Imai-Ogata, N.; Shimowatari, M.; Nagumo, S.; Kawahara, N.; Suemune, H. J. Org. Chem. 2004, 69, 1144
18. Murphy, S. K.; Coulter, M. M.; Dong, V. M. Chem. Sci. (DOI: 10.1039/c1sc00634g).
19. Bedford, R. B.; Coles, S. J.; Hursthouse, M. B.; Limmert, M. E. Angew. Chem., Int. Ed. 2003, 42, 112
20. Bedford, R. B.; Limmert, M. E. J. Org. Chem. 2003, 68, 8669
21. Grünanger, C. U.; Breit, B. Angew. Chem., Int. Ed. 2008, 120, 7456
22. Grünanger, C. U.; Breit, B. Angew. Chem., Int. Ed. 2010, 49, 967
23. Usui, I.; Nomura, K.; Breit, B. Org. Lett. 2011, 13, 612
24. Ueki, Y.; Ito, H.; Usui, I.; Breit, B. Chem.-Eur. J. 2011, 17, 8555
25. Rousseau, G.; Breit, B. Angew. Chem., Int. Ed. 2011, 50, 2450
26. Lightburn, T. E.; Dombrowski, M. T.; Tan, K. L. J. Am. Chem. Soc. 2008, 130, 9210
27. Lightburn, T. E.; De Paolis, O. A.; Cheng, K. H.; Tan, K. L. Org. Lett. 2011, 13, 2686
28. Worthy, A. D.; Joe, C. L.; Lightburn, T. E.; Tan, K. L. J. Am. Chem. Soc. 2010, 132, 14757
29. Tan, K. L. ACS Catal. 2011, 1, 877
30. Khan, H. A.; Kou, K. G. M.; Dong, V. M. Chem. Sci. 2011, 2, 407
31. See ref 6b.
32. Sugihara, T.; Satoh, T.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. 2003, 42, 4672
33. Martinez, R.; Voica, F.; Genet, J-P.; Darses, S. Org. Lett. 2007, 9, 3213
34. The stereochemistry was assigned by comparison to trans- 2-phenyl-3-methyltetrahydrofuran, see: Schmitt, A.; Reiig, H.-U. Eur. J. Org. Chem. 2000, 3893