C2-Symmetric Cu(II) Complexes as Chiral Lewis Acids. Catalytic, Enantioselective Cycloadditions of Silyl Ketenes

Organic Letters

Volumn 3, Issue 13, 2001, Pages 2125-2128

  Evans, David A ^a   Janey, Jacob M ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0001320447     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016096z     Document Type: Article

References (67)

1. (a) For a seminal reference, see; Staudinger, H.; Bereza, S. Ann. 1911, 380, 243-277.
2. (b) For an excellent recent review concerning all aspects of ketene chemistry, see: Tidwell, T. T. Ketenes; John Wiley and Sons: Canada, 1995.
3. Pommier, A.; Pons, J.-M. Synthesis 1993, 441-449.
4. (a) Vederas, J. C.; Ratemi, E. S. Tetrahedron Lett. 1994, 35, 7605-7608.
5. (b) Nelson, S. G.; Spencer, K. L. Angew. Chem., Int. Ed. 2000, 39, 1323-1325.
6. (c) Fujisawa, T.; Ito, T.; Fujimoto, K.; Shimizu, M.; Wynberg, H.; Staring, E. G. J. Tetrahedron Lett. 1997, 38, 1593-1596.
7. (d) Romo, D.; Yang, H. W. J. Org. Chem. 1998, 63, 1344-1347.
8. (e) Fujisawa, T.; Ito, T.; Nishiura, S.; Shimizu, M. Tetrahedron Lett. 1998, 39, 9735-9738.
9. (f) Vederas, J. C.; Arnold, L. D.; May, R. G. J. Am. Chem. Soc. 1988, 110, 2237-2241.
10. (g) Vederas, J. C; Arnold, L. D.; Drover, J. C. G. J. Am. Chem. Soc. 1987, 109, 4649-4659.
11. (a) Hyatt, J. A.; Raynolds, P. W. Org. React. 1994, 45, 159-246.
12. (b) Nelson, S. G.; Wan, Z.; Peelen, T. J.; Spencer, K. L. Tetrahedron Lett. 1999, 40, 6535-6539.
13. (c) Nelson, S. G.; Peelen, T. J.; Wan, Z. Tetrahedron Lett. 1999, 40, 6541-6543.
14. (d) Yamamoto, H.; Maruoka, K.; Concepcion, A. B. Tetrahedron 1995, 51, 4011-4020.
15. (e) Nelson, S. G.; Spencer, K. L. J. Org. Chem. 2000, 65, 1227-1230.
16. (a) Romo, D.; Yang, H. Tetrahedron: Asymmetry 1997, 55, 6403-6434.
17. (b) Cammas, S.; Renard, I.; Boutault, K.; Guerin, P. Tetrahedron: Asymmetry 1993, 4, 1925-1930.
18. Nelson, S. G.; Peelen, T. J.; Wan, Z. J. Am. Chem. Soc. 1999, 121, 9742-9743.
19. Evans, D. A.; Peterson, G. S.; Johnson, J. S.; Barnes, D. M.; Campos, K. R.; Woerpel, K. A. J. Org. Chem. 1998, 63, 4541-4544.
20. (a) Evans, D. A.; Rovis, T.; Johnson, J. S. Pure Appl. Chem. 1999, 71, 1407-1415.
21. (b) Evans, D. A.; Johnson, J. S. Acc. Chem. Res. 2000, 33, 325-335.
22. (a) Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460-6461.
23. (b) Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798-800.
24. (c) Evans, D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481-7484.
25. (d) Evans, D. A.; Barnes, D. M. Tetrahedron Lett. 1997, 38, 57-58.
26. (e) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786-787.
27. (f) Evans, D. A.; Shaughnessy, E. A.; Barnes, D. M. Tetrahedron Lett. 1997, 38, 3193-3194.
28. (g) Davies, I. W.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1996, 37, 1725-1729.
29. (h) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1996, 37, 3815-3819.
30. (a) Evans, D. A.; Johnson, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635-1649.
31. (b) Evans, D. A.; Olhava, E. J.; Johnson, J. S.; Janey, J. M. Angew. Chem., Int. Ed. 1998, 37, 3372-3375.
32. (c) Evans, D. A.; Johnson, J. S.; Burgey, C. S.; Campos, K. R. Tetrahedron Lett. 1999, 40, 2879.
33. (d) Thorhauge, J.; Johannsen, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 1998, 37, 2404-2406.
34. (e) Thorhauge, J.; Johannsen, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 1998, 110, 2543-2546.
35. (f) Evans, D. A.; Johnson, J. S. J. Am. Chem. Soc. 1998, 120, 4895-4896.
36. (g) Johannsen, M.; Jørgensen, K. A. J. Org. Chem. 1995, 60, 5757-5758.
37. (h) Johannsen, M.; Jørgensen, K. A. Tetrahedron 1996, 52, 7321-7328.
38. (i) Ghosh, A. K.; Mathivanen, P.; Cappiello, J.; Krishnan, K. Tetrahedron: Asymmetry 1996, 8, 2165-2169.
39. (a) Evans, D. A.; Murry, J. A. J. Am. Chem. Soc. 1996, 118, 5814-5815.
40. (b) Evans, D. A.; Kozlowski, M. C.; Burgey, C. S.; MacMillan, D. W. C. J. Am. Chem. Soc. 1997, 119, 7893-7894.
41. (c) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686-699.
42. (d) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669-685.
43. Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825.
44. Evans, D. A.; Johnson, D. S. Org. Lett. 1999, 1, 595-598.
45. (a) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994-1995.
46. (b) Evans, D. A.; Willis, M. C.; Johnston, J. N. Org. Lett. 1999, 1, 865-868.
47. Prepared by thermolysis of trimethylsilylethoxyacetylene (see Supporting Information): (a) Shchukouskaya, L.; Pal'chik, R. I. Dokl. Akad. Nauk. 1965, 357-360.
48. (b) Shchukouskaya, L.; Pal'chik, R. I. Dokl. Akad. Nauk. Engl. Ed. 1965, 164, 887-890.
49. (c) Ruden, R. A. J. Org. Chem. 1974, 39, 3607-3608.
50. (a) Pons, J.-M.; Kocienski, P. J.; Dymock, B. W. Chem. Commun. 1996, 1053-1054.
51. (b) Romo, D.; Yang, H. W. Tetrahedron Lett. 1998, 39, 2877-2880.
52. Liu, R.; Marra, R. M.; Tidwell, T. T. J. Org. Chem. 1996, 61, 6227-6232.
53. Fleming, I.; Henning, R., Parker, D. C.; Flaut, H. E.; Sanderson, P. E. J. J. Chem. Soc., Perkin Trans. 1 1995, 317-337.
54. Previous work with the Cu(II)-bis(oxazoline)-catalyzed Mukaiyama aldol reaction between silylketene acetals and pyruvate esters has shown that the ester substituent has little influence on the stereochemical course of the reaction, see ref 11c.
55. 2 (4g).
56. For synthesis of the PyBox ligands, see: Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500-508.
57. The absolute configuration was determined by acyl ring opening of 16 with EtOH to yield the previously reported ethyl ester, see ref 11d and Supporting Information.
58. 1H NMR and chemical correlation (see Supporting Information).
59. (a) Ghosez, L.; Marchand-Brynaert, J. in Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 86-89.
60. (b) Krabbenhoft, H. O. J. Org. Chem. 1978, 43, 1305-1311.
61. (c) Yamabe, S.; Minato, T.; Osamura, Y. J. Chem. Commun. 1993, 450-452.
62. (d) Lecea, B.; Arrieta, A.; Roa, G.; Ugalde, J. M.; Cossio, F. P. J. Am. Chem. Soc. 1994, 116, 9613-9619.
63. (e) Baldwin, J. E.; Kapecki, J. A. J. Am. Chem. Soc. 1970, 92, 4868-4873.
64. (f) Baldwin, J. E.; Kapecki, J. A. J. Am. Chem. Soc. 1970, 92, 4874-4879.
65. It has also been suggested that some ketene-alkene [2 + 2] cycloadditions proceed through a stepwise zwitterionic mechanism, see: (a) Frey, H. M.; Isaacs, N. J. J. Chem. Soc. B 1970, 830-832.
66. (b) Reference 1b.
67. Cammas, S.; Renard, I.; Boutault, K.; Guerin, P. Tetrahedron: Asymmetry 1993, 4, 1925-1930.