Platinum(II)-catalyzed reaction of γ,δ-ynones with alkenes for the construction of 8-oxabicyclo[3.2.1]octane skeletons: Generation of platinum-containing carbonyl ylides from acyclic precursors

Angewandte Chemie - International Edition

Volumn 47, Issue 26, 2008, Pages 4903-4905

  Kusama, Hiroyuki ^a   Ishida, Kento ^a   Funami, Hideaki ^a   Iwasawa, Nobuharu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Carbene ligands; Carbonyl ylides; Cycloaddition; Platinum; Ynones

Indexed keywords

CHEMICAL REACTIONS; ETHERS; HYDROCARBONS; HYDROGEN; OLEFINS; ORGANIC COMPOUNDS; PLATINUM; STYRENE;

CARBENE LIGANDS; CARBONYL YLIDES; CYCLOADDITION; YNONES;

CARBONYLATION;

EID: 53549135506     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705129     Document Type: Article

References (52)

1. a) N. Iwasawa, M. Shido, H. Kusama, J. Am. Chem. Soc. 2001, 123, 5814-5815;
2. b) H. Kusama, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2002, 124, 11592-11593;
3. c) H. Kusama, H. Funami, J. Takaya, N. Iwasawa, Org. Lett. 2004, 6, 605-608;
4. d) J. Takaya, H. Kusama, N. Iwasawa, Chem. Lett. 2004, 33, 16-17;
5. e) H. Kusama, H. Funami, M. Shido, Y. Hara, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2005, 127, 2709-2716;
6. f) H. Kusama, Y. Miyashita, J. Takaya, N. Iwasawa, Org. Lett. 2006, 8, 289-292;
7. g) H. Kusama, Y. Suzuki, J. Takaya, N. Iwasawa, Org. Lett. 2006, 8, 895-897;
8. h) H. Kusama, H. Funami, N. Iwasawa, Synthesis 2007, 2014-2024.
9. For other examples of the cycloaddition of metal-containing benzopyrylium-type intermediates, see: a) N. Asao, K. Takahashi, S. Lee, T. Kasahara, Y. Yamamoto, J. Am. Chem. Soc. 2002, 124, 12650-12651;
10. b) N. Asao, T. Nogami, S. Lee, Y. Yamamoto, J. Am. Chem. Soc. 2003, 125, 10921-10925;
11. c) N. Asao, T. Kasahara, Y. Yamamoto, Angew. Chem. 2003, 115, 3628-3630;
12. Angew. Chem. Int. Ed. 2003, 42, 3504-3506;
13. d) N. Asao, H. Aikawa, Y. Yamamoto, J. Am. Chem. Soc. 2004, 126, 7458-7459;
14. e) N. Asao, K. Sato, Menggenbateer, Y. Yamamoto, J. Org. Chem. 2005, 70, 3682-3685;
15. f) N. Asao, H. Aikawa, J. Org. Chem. 2006, 71, 5249-5253;
16. g) N. Asao, K. Sato, Org. Lett. 2006, 8, 5361-5363;
17. h) S. Shin, A. K. Gupta, C. Y. Rhim, C. H. Oh, Chem. Commun. 2005, 4429-4431;
18. i) N. Kim, Y. Kim, W. Park, D. Sung, A. K. Gupta, C. H. Oh, Org. Lett. 2005, 7, 5289-5291;
19. j) A. K. Gupta, C. Y. Rhim, C. H. Oh, R. S. Mane, S.-H. Han, Green Chem. 2006, 8, 25-28;
20. k) G. Dyker, D. Hildebrandt, J. Org. Chem. 2005, 70, 6093-6096;
21. l) D. Hildebrandt, W. Hüggenberg, M. Kanthak, T. Plöger, I. M. Müller, G. Dyker, Chem. Commun. 2006, 2260-2261;
22. m) C. H. Oh, J. H. Ryu, H. I. Lee, Synlett 2007, 2337-2342;
23. n) J. Zhu, A. R. Germain, J. A. Porco, Jr, Angew. Chem. 2004, 116, 1259-1263;
24. Angew. Chem. Int. Ed. 2004, 43, 1239-1243;
25. o) A. B. Beeler, S. Su, C. A. Singleton, J. A. Porco, Jr., J. Am. Chem. Soc. 2007, 129, 1413-1419.
26. For recent examples of addition reactions of nucleophiles to metal-containing zwitterionic intermediates, see: a) N. T. Patil, H. Wu, Y. Yamamoto, J. Org. Chem. 2005, 70, 4531-4534;
27. b) N. Asao, S. Yudha, T. Nogami, Y. Yamamoto, Angew. Chem. 2005, 117, 5662-5664;
28. Angew. Chem. Int. Ed. 2005, 44, 5526-5528;
29. c) X. Yao, C.-J. Li, Org. Lett. 2006, 8, 1953-1955;
30. d) R. Yanada, S. Obika, H. Kono, Y. Takemoto, Angew. Chem. 2006, 118, 3906-3909;
31. Angew. Chem. Int. Ed. 2006, 45, 3822-3825;
32. e) J. Zhang, H.-G. Schmalz, Angew. Chem. 2006, 118, 6856-6859;
33. Angew. Chem. Int. Ed. 2006, 45, 6704-6707;
34. f) C. H. Oh, R. Reddy, A. Kim, C. Y. Rhim, Tetrahedron Lett. 2006, 47, 5307-5310;
35. g) Y. Liang, Y.-X. Xie, J.-H. Li, Synthesis 2007, 400-406.
36. For reviews on cycloaddition reactions of metal-containing zwitterionic intermediates, see: a) H. Kusama, N. Iwasawa, Chem. Lett. 2006, 35, 1082-1087;
37. b) N. Asao, Synlett 2006, 1645-1656.
38. Ohe and co-workers studied extensively the synthesis of furylcarbene complexes through the 5-exo-dig cyclization of carbonyl enyne compounds; for a review, see: K. Miki, S. Uemura, K. Ohe, Chem. Lett. 2005, 34, 1068-1073.
39. For recent reviews on platinum(II)-catalyzed reactions, see: a) C. Nevado, A. M. Echavarren, Synthesis 2005, 167-182;
40. b) C. Bruneau, Angew. Chem. 2005, 117, 2380-2386;
41. Angew. Chem. Int. Ed. 2005, 44, 2328-2334;
42. c) C. Nieto-Oberhuber, S. López, E. Jiménez-Núnez, A. M. Echavarren, Chem. Eur. J. 2006, 12, 5916-5923;
43. d) A. Fúrstner, P. W. Davies, Angew. Chem. 2007, 119, 3478-3519;
44. Angew. Chem. Int. Ed. 2007, 46, 3410-3449;
45. e) J. Marco-Contelles, E. Soriano, Chem. Eur. J. 2007, 13, 1350-1357.
46. For other recent examples of 1,2-alkyl migrations in platinum-carbene intermediates, see: a) J. Sun, M. P. Conley, L. Zhang, S. A. Kozmin, J. Am. Chem. Soc. 2006, 128, 9705-9710;
47. b) H. Funami, H. Kusama, N. Iwasawa, Angew. Chem. 2007, 119, 927-929;
48. Angew. Chem. Int. Ed. 2007, 46, 909-911.
49. [4b] of a platinum-containing zwitterionic intermediate 3 with n-butyl vinyl ether to give the oxonium intermediate 11 directly. However, at present, we believe the [3+2]cyclo addition pathway to be the most plausible pathway in the present reaction on the basis of the experimental result shown in Table 1, entry 3. If the reaction proceeds through a [4+2]cyclo addition, a mixture of 2 and 8 should form from the oxonium intermediate 11 owing to the pseudosymmetric structure of 11. We are currently carrying out calculations of the reaction pathways to obtain further information on the exact mechanism of this reaction. For a discussion, see: B. F. Straub, Chem. Commun. 2004, 1726-1728. (Chemical Equation Presented)
50. It is likely that the 1,2-hydrogen-atom shift to the electron-deficient carbene carbon atom has a hydride-shift character, and that the electron-donating effect of the substituent at the propargylic position of substrates 1 (or the nBuO substituent in 12 a) promotes the 1,2-hydrogen-atom shift.
51. For reviews on the [3+2]cycloa ddition of carbonyl ylide species derived from α-diazoketone derivatives with a Rh catalyst, see: a) G. Mehta, S. Muthusamy, Tetrahedron 2002, 58, 9477-9504;
52. b) A. Padwa, Helv. Chim. Acta 2005, 88, 1357-1374.