Synthesis of α-methyl ketones by a selective, iridium-catalyzed cyclopropanol ring-opening reaction

Tetrahedron Letters

Volumn 51, Issue 51, 2010, Pages 6726-6729

  Ziegler, Daniel T ^a   Steffens, Andrew M ^a   Funk, Timothy W ^a  

^a GETTYSBURG COLLEGE   (United States)

Author keywords

Carbon carbon bond cleavage; Cyclopropane; Cyclopropanol; Iridium; Ring opening

Indexed keywords

ALPHA METHYL KETONE DERIVATIVE; CYCLOPROPANOL; CYCLOPROPYL SILYL ETHER DERIVATIVE; ETHER DERIVATIVE; IRIDIUM; KETONE DERIVATIVE; PROPANOL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ISOMERIZATION; RING OPENING; SYNTHESIS;

EID: 78649324181     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.10.067     Document Type: Article

References (45)

1. For reviews see: O.G. Kulinkovich Chem. Rev. 103 2003 2597
2. D.H. Gibson, and C.H. DePuy Chem. Rev. 74 1974 605
3. H. Rinderhagen, P.A. Waske, and J. Mattay Tetrahedron 62 2006 6589
4. S. Murai, I. Ryu, and N. Sonoda J. Organomet. Chem. 250 1983 121
5. L.A. Paquette Chem. Rev. 86 1986 733
6. M. Yu, and B.L. Pagenkopf Tetrahedron 61 2005 321
7. H.N.C. Wong, M.-Y. Hon, C.-W. Tse, Y.-C. Yip, J. Tanko, and T. Hudlicky Chem. Rev. 89 1989 165
8. H.-U. Reissig, and R. Zimmer Chem. Rev. 103 2003 1151
9. For other reports see: O.L. Epstein, S. Lee, and J.K. Cha Angew. Chem., Int. Ed. 45 2006 4988
10. I.L. Lysenko, H.-S. Oh, and J.K. Cha J. Org. Chem. 72 2007 7903
11. H.G. Lee, I.L. Lysenko, and J.K. Cha Angew. Chem., Int. Ed. 46 2007 3326
12. A.B. Charette, and A. Beauchemin Org. React. 2004 1
13. J.M. Conia Pure Appl. Chem. 43 1975 317
14. J. Furukawa, N. Kawabata, and J. Nishimura Tetrahedron 24 1968 53
15. For recent examples of cyclopropanol ring-opening reactions, see: D.H. Churykau, and O.G. Kulinkovich Synlett 2006 3427
16. K.A. Keaton, and A.J. Phillips Org. Lett. 9 2007 2717
17. J.P. Markham, S.T. Staben, and F.D. Toste J. Am. Chem. Soc. 127 2005 9708
18. B.M. Trost, J. Xie, and N. Maulide J. Am. Chem. Soc. 130 2008 17258
19. K. Nomura, and S. Matsubara Chem. Eur. J. 16 2010 703
20. G. Stork, P. Rosen, and N.L. Goldman J. Am. Chem. Soc. 83 1961 2965
21. H.O. House, M. Gall, and H.D. Olmstead J. Org. Chem. 36 1971 2361
22. T. Hatakeyama, S. Ito, H. Yamane, M. Nakamura, and E. Nakamura Tetrahedron 63 2007 8440
23. For more details see Ref. 1 in S. Saito, M. Ito, and H. Yamamoto J. Am. Chem. Soc. 119 1997 611
24. Silyl cyclopropyl ethers also afford α-methyl ketones under basic hydrolysis conditions; see Ref. 2b.
25. M. Shan, and G.A. O'Doherty Org. Lett. 10 2008 3381
26. M. Shan, and G.A. O'Doherty Synthesis 2008 3171
27. J.O. Hoberg, and P.W. Jennings Organometallics 15 1996 3902
28. For an application in total synthesis, see: O.L. Epstein, and J.K. Cha Angew. Chem., Int. Ed. 44 2005 121
29. S.-H. Kim, M.J. Sung, and J.K. Cha Org. Synth. 80 2003 111
30. J. Lee, H. Kim, and J.K. Cha J. Am. Chem. Soc. 118 1996 4198
31. 1H NMR spectrum matched those published for alkene 4a: S.-M. Lu, and C. Bolm Angew. Chem., Int. Ed. 47 2008 8920
32. Palladium-catalyzed oxidative ring-openings of cyclopropanols are known: S.-B. Park, and J.K. Cha Org. Lett. 2 2000 147
33. H. Okumoto, T. Jinnai, H. Shimizu, Y. Harada, H. Mishima, and A. Suzuki Synlett 2000 629
34. This would be a platinum analogue of the known palladium-catalyzed oxidative ring-opening of cyclopropanols. See Ref. 10.
35. K. Ikura, I. Ryu, N. Kambe, and N. Sonoda J. Am. Chem. Soc. 114 1992 1520
36. K. Ikura, I. Ryu, A. Ogawa, N. Sonoda, S. Harada, and N. Kasai Organometallics 10 1991 528
37. D. Griller, and K.U. Ingold Acc. Chem. Res. 13 1980 317
38. M. Mkosza, and A. Kwast Eur. J. Org. Chem. 2004 2125
39. M. Newcomb, A.G. Glenn, and W.G. Williams J. Org. Chem. 54 1989 2675
40. V.W. Bowry, J. Lusztyk, and K.U. Ingold J. Am. Chem. Soc. 113 1991 5687
41. K.-I. Fujita, and R. Yamaguchi Synlett 2005 560
42. K.-I. Fujita, S. Furukawa, and R. Yamaguchi J. Organomet. Chem. 649 2002 289
43. B. Jiang, Y. Feng, and E.A. Ison J. Am. Chem. Soc. 130 2008 14462
44. For a proposed Ir(V) metallacyclobutane intermediate, see: M.R. Anstey, C.M. Yung, J. Du, and R.G. Bergman J. Am. Chem. Soc. 129 2007 776
45. For Ir(III) metallacyclobutanes, see: P.W. Jennings, and L.L. Johnson Chem. Rev. 94 1994 2241