Highly diastereoselective gold- Or copper-catalyzed formal [4+3] cycloaddition of 1-(1-Alkynyl) cyclopropyl ketones and nitrones

Chemistry - A European Journal

Volumn 15, Issue 36, 2009, Pages 8975-8978

  Bai, Yu ^a   Fang, Jie ^a   Ren, Jun ^a   Wang, Zhongwen ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

Alkynes; Cycloaddition; Cyclopropanes; Domino reactions; Lewis acids

Indexed keywords

ALKYNES; ALKYNYLS; CYCLOPROPANES; CYCLOPROPYL KETONES; DIASTEREOSELECTIVE; DICHLOROETHANE; DOMINO REACTIONS; LEWIS ACID; LEWIS ACIDS; NITRONES; ONE POT; THREE-COMPONENT;

ACETYLENE; ACIDS; CLUSTERING ALGORITHMS; PROPANE; REACTION KINETICS; STEREOSELECTIVITY;

KETONES;

ALKYNE; COPPER; CYCLOPROPANE DERIVATIVE; GOLD; KETONE; ORGANOMETALLIC COMPOUND;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

ALKYNES; CATALYSIS; COPPER; CRYSTALLOGRAPHY, X-RAY; CYCLOPROPANES; GOLD; KETONES; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 70349158108     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901133     Document Type: Article

References (66)

1. Selected reviews on some typical cycloadditions, see: a) Cycloaddition Reactions in Organic Synthesis (Eds.: S. Kobayashi, K. A. Jorgensen), Wiley-VCH, Weinheim, 2001;
2. b)Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products: The Chemistry of Heterocyclic Compounds, Vol.59 (Eds.: A. Padwa, W. H. Pearson), Wiley, New York, 2002;
3. c) The Diels-Alder Reaction: Selected Practical Methods (Eds.: F. FringuelIi, A. Taticchi), Wiley, New York, 2002.
4. Selected reviews on tandem reactions, see: a) L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137;
5. Angew. Chem. Int. Ed. Engl. 1993, 32, 131;
6. b) L.F. Tietze, Chem. Rev. 1996, 96, 115;
7. c) P.J. Parsons, C. S. Penkett, A.J. Shell, Chem. Rev. 1996, 96, 195;
8. d) R. A. Bunce, Tetrahedron 1995, 51, 13103;
9. e) K. C Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292;
10. Angew. Chem. Int. Ed. 2006, 45, 7134;
11. f) H. Pellissier, Tetrahedron 2006, 62, 1619;
12. g) H. Pellissier, Tetrahedron 2006, 62, 2143.
13. R. Robinson, J. Chem. Soc. 1917, 111, 762.
14. For reviews, please see: a) S. Danishefsky, Acc. Chem. Res. 1979, 12, 66;
15. b) H. N. C Wong, M. Y Hon, C W. Tse, Y C Yip, Chem. Rev. 1989, 89, 165;
16. c) H.-U. Reissig, R. Zimmer, Chem. Rev. 2003, 103, 1151;
17. d)M. Yu, B. L. Pagenkopf, Tetrahedron 2005, 61, 321;
18. e) E. Wenkert, Ace. Chem. Res. 1980, 13, 27;
19. f) O. G. Kulinkovich, Chem. Rev. 2003, 103, 2597;
20. g) L. A. Paquette, Chem. Rev. 1986, 86, 733;
21. h) D. Agrawal, V. K. Yadav, Chem. Commun. 2008, 6471.
22. a) A. S. K. Hashmi, Angew. Chem. 1995, 107, 1749;
23. Angew. Chem. Int. Ed. Engl. 1995, 34, 1581;
24. b) A. S. K. Hashmi, T. L. Ruppert, T. Knofel, J. W. Bats, J. Org. Chem. 1997, 62, 7295;
25. c) J. A. Marshall, E. M. Wallace, P. S. Coan, J. Org. Chem. 1995, 60, 796;
26. d) J. A. Marshall, G. S. Bartley, J. Org. Chem. 1994, 59, 7169;
27. e) J. A. Marshall, X. J. Wang, J. Org. Chem. 1991, 56, 960;
28. f) J. A. Marshall, E. D. Robinson, J. Org. Chem. 1990, 55, 3450;
29. g) S. Ma, L. Li, Org. Lett. 2000, 2, 941;
30. h) S. Ma, J. Zhang, L. Lu, Chem. Eur. J. 2003, 9, 2447;
31. i) S. Ma, Z. Yu, Angew. Chem. 2002, 114, 1853;
32. Angew. Chem. Int. Ed. 2002, 41, 1775.
33. a) Y. Fukuda, H. Shiragami, K. Utimoto, H. Nozaki, J. Org. Chem. 1991, 56, 5816;
34. b) A. V. Kel'in, V. Gevorgyan, J. Org. Chem. 2002, 67, 95;
35. c)A. S. K. Hashmi, L. Schwarz, J.-H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382;
36. Angew. Chem. Int. Ed. 2000, 39, 2285;
37. d) A. W Sromek, A. V. Kel'in, V. Gevorgyan, Angew. Chem. 2004, 116, 2330;
38. Angew. Chem. Int. Ed. 2004, 43, 2280;
39. e) M. H. Suhre, M. Reif, S. F. Kirsch, Org. Lett. 2005, 7, 3925.
40. a) T. Yao, X. Zhang, R. C. Larock, J. Am. Chem. Soc. 2004, 126, 11164;
41. b) N. T. Patil, H. Wu, Y. Yamamoto, J. Org. Chem. 2005, 70, 4531.
42. a) S. Ma, J. Zhang, Angew. Chem. 2003, 115, 193;
43. Angew. Chem. Int. Ed. 2003, 42, 183;
44. b) S. Ma, L. Lu, J. Zhang, J. Am. Chem. Soc. 2004, 126, 9645.
45. a) A. Padwa, J. M. Kassir, S. L. Xu, J. Org. Chem. 1991, 56, 6971;
46. b) S. Ma, J. Zhang, J. Am. Chem. Soc. 2003, 125, 12386.
47. J. Zhang, H.-G. Schmalz, Angew. Chem. 2006, 118, 6856;
48. Angew. Chem. Int. Ed. 2006, 45, 6704.
49. a) G. Zhang, X. Huang, G. Li, L. Zhang, J. Am. Chem. Soc. 2008, 130, 1814;
50. b) G. Li, X. Huang, L. Zhang, J. Am. Chem. Soc. 2008, 130, 6944.
51. I to build 5,6-dihydrocyclopenta[c]furanones, see: Y Zhang, Z. Chen, Y Xiao, J. Zhang, Chem. Eur. J. 2009, 15, 5208.
52. a) I. S. Young, M. A. Kerr, Angew. Chem 2003, 115, 3131;
53. Angew. Chem. Int. Ed. 2003, 42, 3023;
54. b) I. S. Young, M. A. Kerr, Org. Lett. 2004, 6, 139;
55. c) K. Sapeta, M. A. Kerr, J. Org. Chem. 2007, 72, 8597;
56. d) M. P. Sibi, Z. Ma, C P Jasperse, J. Am. Chem. Soc. 2005, 127, 5764;
57. e) B. Hu, J. Zhu, S. Xing, J. Fang, D. Du, Z. Wang, Chem. Eur. J. 2009, 15, 324.
58. R. Shintani, M. Murakami, T. Hayashi, J. Am. Chem. Soc. 2007, 129, 12356.
59. 1,2-Oxazepine skeleton exists in several bioactive compounds, see: a) T. Kurihara, Y Sakamoto, H. Matsumoto, N Kawabata, S. Harusawa, R. Yoneda, Chem. Pharm. Bull. 1994, 42, 475;
60. b) J. I. Levin, A.M. Venkatesan, P. S. Chan, T.K. Bailey, G. Vice, J. Coupet, Bioorg. Med. Chem. Lett. 1994, 4, 1819;
61. c) I. Takáno, I. Yasuda, M. Nishijima, Y Hitotsuyanagi, K. Takeya, H. Itokawa, J. Org. Chem. 1997, 62, 8251.
62. A. Saini, S. Kumar, J. S. Sandhu, Synlett 2006, 395.
63. Structures of 31 and 3p were confirmed by the single-crystal X-ray diffraction analysis. CCDC 715149 and 715150 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
64. X. Huang, W. Fu, M. Miao, Tetrahedron Lett. 2008, 49, 2359.
65. R. Fang, C. Y Su, C Zhao, D. L. Phillips, Organometallics 2009, 28, 741.
66. 2 for this three-component reaction gave dissatisfied result.