Enantioenriched synthesis of cyclopropenes with a quaternary stereocenter, versatile building blocks

Journal of the American Chemical Society

Volumn 133, Issue 2, 2011, Pages 170-171

  Uehara, Misaki ^a   Suematsu, Hidehiro ^a   Yasutomi, Yoichi ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BUILDING BLOCKES; CARBENOIDS; CYCLOPROPENES; DIAZO COMPOUNDS; DIAZOACETAMIDE; ENANTIOSELECTIVE; FUNCTIONALIZED; QUATERNARY CARBON; QUATERNARY STEREOCENTERS;

IRIDIUM;

2,2,2 TRIFLUORO 1 PHENYL 1 DIAZOETHANE; ACETIC ACID DERIVATIVE; ALPHA CYANO ALPHA DIAZOACETAMIDE; ALPHA PHENYL ALPHA DIAZOPHOSPHONATE; CARBENOID; CARBON; ETHANE; IRIDIUM; PROPYLENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; COMPLEX FORMATION; DONOR; ENANTIOSELECTIVITY; PRECURSOR; SUBSTITUTION REACTION; SYNTHESIS;

CATALYSIS; CYCLOPROPANES; IRIDIUM; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 78651386359     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1089217     Document Type: Article

References (36)

1. Marek, I., Simaan, S., and Masarwa, A. Angew. Chem. 2007, 119, 3963;
2. Angew. Chem., Int. Ed. 2007, 46, 7364
3. Rubin, M., Rubina, M., and Gevorgyan, V. Chem. Rev. 2007, 107, 3117
4. Rubin, M., Rubina, M., and Gevorgyan, V. Synthesis 2006, 8, 1221
5. Simaan, S., Masarwa, A., Zohar, E., Stanger, A., Bertus, P., and Marek, I. Chem. - Eur. J. 2009, 15, 8449
6. Hoveyda, A. H., Lombardi, P. J., O'Brien, R. V., and Zhugralin, A. R. J. Am. Chem. Soc. 2009, 131, 8378
7. Tarwade, V., Liu, X., Yan, N., and Fox, J. M. J. Am. Chem. Soc. 2009, 131, 5382
8. DeAngelis, A., Taylor, M. T., and Fox, J. M. J. Am. Chem. Soc. 2009, 131, 1101
9. Sherrill, W. M. and Rubin, M. J. Am. Chem. Soc. 2008, 130, 13804
10. Yan, N., Liu, X., and Fox, J. M. J. Org. Chem. 2008, 73, 563
11. Weatherhead-Kloster, R. A. and Corey, E. J. Org. Lett. 2006, 8, 171
12. Protopopova, M. N., Doyle, M. P., Müller, P., and Ene, D. J. Am. Chem. Soc. 1992, 114, 2755
13. Doyle, M. P., Protopopova, M., Müller, P., Ene, D., and Shapiro, E. A. J. Am. Chem. Soc. 1994, 116, 8492
14. Doyle, M. P., Ene, D., Peterson, C. S., and Lynch, V. Angew. Chem., Int. Ed. 1999, 38, 700
15. Müller, P. and Imogaï, H. Tetrahedron: Asymmetry 1998, 9, 4419
16. Imogaï, H., Bernardinelli, G., Gränicher, C., Moran, M., Rossier, J.-C., and Müller, P. Helv. Chim. Acta 1998, 81, 1754
17. Lou, Y., Horikawa, M., Kloster, R. A., Hawryluk, N. A., and Corey, E. J. J. Am. Chem. Soc. 2004, 126, 8916
18. Lou, Y., Remarchuk, T. P., and Corey, E. J. J. Am. Chem. Soc. 2005, 127, 14223
19. Davies, H. M. L. and Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861
20. Davies, H. M. L. and Lee, G. H. Org. Lett. 2004, 6, 1233
21. Christoffers, J. and Baro, A. Adv. Synth. Catal. 2005, 347, 1473
22. Kanchiku, S., Suematsu, H., Matsumoto, K., Uchida, T., and Katsuki, T. Angew. Chem., Int. Ed. 2007, 46, 3889
23. Suematsu, H., Kanchiku, S., Uchida, T., and Katsuki, T. J. Am. Chem. Soc. 2008, 130, 10327
24. Ichinose, M., Suematsu, H., and Katsuki, T. Angew. Chem., Int. Ed. 2009, 48, 3121
25. Suematsu, H. and Katsuki, T. J. Am. Chem. Soc. 2009, 131, 14218
26. Yasutomi, Y., Suematsu, H., and Katsuki, T. J. Am. Chem. Soc. 2010, 132, 4510
27. See the Supporting Information (Table S-1).
28. Most reactions in Tables 1 and 2 had a similar level of enantioselectivity either in DCM or in toluene. For example, 85% ee and 96% ee were obtained in the reactions of phenylacetylene with α-phenyl-α- diazophosphonate and 1-phenyl-2,2,2-trifluoromethyldiazoethane, respectively (cf. Table 2, entries 9 and 13).
29. Asymmetric cyclopropanation with α-cyano-α-diazoacetamides has been reported
30. Marcoux, D., Azzi, S., and Charette, A. B. J. Am. Chem. Soc. 2009, 131, 6970
31. Zhu, S., Xu, X., Perman, J. A., and Zhang, X. P. J. Am. Chem. Soc. 2010, 132, 12796 and references cited therein
32. See the Supporting Information (Table S-2).
33. The cyclopropenation of 1-decyne with benzyl diazoacetate using 5 as a catalyst proceeds with 80% ee.
34. For the cyclopropanation reactions using diazo compounds bearing a phosphonate or trifluoromethyl group, see Reddy, R. P., Lee, G. H., and Davies, H. M. L. Org. Lett. 2006, 8, 3437
35. Denton, J. R., Sukumaran, D., and Davies, H. M. L. Org. Lett. 2007, 9, 2625
36. Müller, P., Grass, S., Shahi, S. P., and Bernardinelli, G. Tetrahedron 2004, 60, 4755