Asymmetric bisboranes as bidentate catalysts for carbonyl substrates

Organic Letters

Volumn 11, Issue 3, 2009, Pages 713-715

  Rodriguez, Andrew A ^a   Zhao, Carrie ^a   Shea, Kenneth J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE; KETONE; LIGAND; OXAZABOROLIDINONE; SINGLE HETEROCYCLIC RINGS;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

BORANES; CATALYSIS; HETEROCYCLIC COMPOUNDS, 1-RING; KETONES; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 60849125130     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802793k     Document Type: Article

References (32)

1. Shibasaki, M.; Yamamoto, Y. Multimetallic Catalysts in Organic Synthesis; Wiley-VCH: Weinheim, 2004.
2. (a) Mitic, N.; Smith, S. J.; Neves, A.; Guddat, L. W.; Gahan, L. R.; Schlenk, G. Chem. Rev. 2006, 106, 3338-3363.
3. (b) Wilcox, D. E. Chem. Rev. 1996, 96, 2435-2458.
4. (a) Matsunaga, S.; Shibasaki, M. Bull. Chem. Soc. Jpn. 2008, 81, 60-75.
5. (b) Ma, J.-A.; Cahard, D. Angew. Chem., Int. Ed. 2004, 43, 4566-4583.
6. (a) Ooi, T.; Takahashi, M.; Yamada, M.; Tayama, K.; Omoto, K.; Maruoka, K. J. Am. Chem. Soc. 2004, 126, 1150-1160.
7. (b) Saito, A.; Yanai, H.; Taguchi, T. Tetrahedron Lett. 2004, 45, 9439-9442.
8. (c) Saito, A.; Ito, H.; Taguchi, T. Org. Lett. 2002, 4, 4619-4621.
9. (d) Abe, N.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1999, 40, 5369-5372.
10. (e) Ooi, T.; Saito, A.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3745-3748.
11. (a) Hashimoto, T.; Omote, M.; Kano, T.; Maruoka, K. Org. Lett. 2007, 9, 4805-4808.
12. (b) Hanawa, H.; Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 1708-1709.
13. (c) Oh, T.; Lopez, P.; Reilly, M. Eur. J. Org. Chem. 2000, 2901-2903.
14. (d) Reilly, M.; Oh, T. Tetrahedron Lett. 1995, 36, 221-224.
15. Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; von Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594.
16. (a) Singh, R. S.; Harada, T. Eur. J. Org. Chem. 2005, 3433-3435.
17. (b) Ishihara, K.; Yamamoto, H. Eur. J. Org. Chem. 1999, 527-538.
18. Examples of asymmetric Diels-Alder reactions of simple α,β-unsaturated ketones and esters: (a) Singh, R. S.; Adachi, S.; Tanaka, R; Yamauchi, T.; Inui, C.; Harada, T. J. Org. Chem. 2008, 73, 212-218.
19. (b) Futatsugi, K.; Yamamoto, H. Angew. Chem., Int. Ed. 2005, 44, 1484-1487.
20. (c) Hawkins, J. M.; Nambu, M.; Loren, S. Org. Lett. 2003, 5, 4293-4295.
21. (d) Ryu, D. H.; Lee, T. W.; Corey, E. J. J. Am. Chem. Soc. 2002, 124, 9992-9993.
22. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458-2460.
23. 2O in the gas phase is exothermic: LePage, T. J.; Wiberg, K. B. J. Am. Chem. Soc. 1988, 110, 6642-6650.
24. (a) Wuest, J. D. Acc. Chem. Res. 1999, 32, 81-89.
25. (b) Tshinkl, M.; Schier, A.; Riede, J.; Gabbai, F. P. Organometallics 1999, 18, 1747-1753.
26. (c) Vaugeois, J.; Wuest, J. D. J. Am. Chem. Soc. 1998, 120, 13016-13022.
27. (d) Vaugeois, J.; Simard, M.; Wuest, J. D. Coord. Chem. Rev. 1995, 145, 55-73.
28. (e) Sharma, V.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 1992, 114, 7931-7933.
29. Harada, T.; Yamamoto, Y.; Kusukawa, T. Chem. Commun. 2005, 859-861.
30. See Supporting Information for all complete computational data.
31. Kelly, T. R.; Maity, S. K.; Meghani, P.; Chandrakumar, N. S. Tetrahedron Lett. 1989, 30, 1357-1360.
32. Enantioenriched sample prepared using MacMillan's catalyst and compared to our sample by chiral HPLC (Chiralcel AS column): Ahrendt, K. A.; Berths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243-4244.