Asymmetric synthesis using ketenes

Tetrahedron

Volumn 59, Issue 20, 2003, Pages 3545-3565

  Orr, Robert K ^a   Calter, Michael A ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

Asymmetric synthesis; Ketenes; Organic molecules

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; ALKALOID DERIVATIVE; ALKENE DERIVATIVE; ALPHA HALOCARBOXYLATE; CARBOXYLIC ACID DERIVATIVE; IMINE; KETENE DERIVATIVE; LEWIS ACID; METAL COMPLEX; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; BINDING AFFINITY; CATALYSIS; CATALYST; CHEMICAL PARAMETERS; CHEMICAL REACTION; CINCHONA; CYCLOADDITION; PRIORITY JOURNAL; SYNTHESIS;

CINCHONA;

EID: 0037539910     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00491-5     Document Type: Article

References (70)

1. (a) Staudinger H. Ber. 38:1905;1735-1739.
2. (b) Staudinger H. Liebigs Ann. Chem. 356:1907;51-123.
3. Reviews: General Ketene Chemistry: (a) Tidwell T.T. Acc. Chem. Res. 9:1990;273-279. Cycloadditions of Ketenes: (b) Hyatt J.A., Raynolds P.W. Org. React. 45:1994;159-646. Cycloadditions of Ketenes and Aldehydes: (c) Yang H.W., Romo D. Tetrahedron. 55:1999;6403-6434. Cycloadditions of Ketenes and Aldehydes: (d) Palomo C., Aizpurua J.M., Iñaki G., Oiarbide M. Eur. J. Org. Chem. 1999;3223-3235.
4. Reviews: General Ketene Chemistry: (a) Tidwell T.T. Acc. Chem. Res. 9:1990;273-279. Cycloadditions of Ketenes: (b) Hyatt J.A., Raynolds P.W. Org. React. 45:1994;159-646. Cycloadditions of Ketenes and Aldehydes: (c) Yang H.W., Romo D. Tetrahedron. 55:1999;6403-6434. Cycloadditions of Ketenes and Aldehydes: (d) Palomo C., Aizpurua J.M., Iñaki G., Oiarbide M. Eur. J. Org. Chem. 1999;3223-3235.
5. Reviews: General Ketene Chemistry: (a) Tidwell T.T. Acc. Chem. Res. 9:1990;273-279. Cycloadditions of Ketenes: (b) Hyatt J.A., Raynolds P.W. Org. React. 45:1994;159-646. Cycloadditions of Ketenes and Aldehydes: (c) Yang H.W., Romo D. Tetrahedron. 55:1999;6403-6434. Cycloadditions of Ketenes and Aldehydes: (d) Palomo C., Aizpurua J.M., Iñaki G., Oiarbide M. Eur. J. Org. Chem. 1999;3223-3235.
6. Reviews: General Ketene Chemistry: (a) Tidwell T.T. Acc. Chem. Res. 9:1990;273-279. Cycloadditions of Ketenes: (b) Hyatt J.A., Raynolds P.W. Org. React. 45:1994;159-646. Cycloadditions of Ketenes and Aldehydes: (c) Yang H.W., Romo D. Tetrahedron. 55:1999;6403-6434. Cycloadditions of Ketenes and Aldehydes: (d) Palomo C., Aizpurua J.M., Iñaki G., Oiarbide M. Eur. J. Org. Chem. 1999;3223-3235.
7. (a) Tamai Y., Someya M., Fukumoto J., Miyano S. J. Chem. Soc., Perkin. Trans. 1. 1994;1549-1550.
8. (b) Tamai Y., Yoshiwara H., Someya M., Fukumoto J., Miyano S. J. Chem. Soc., Chem. Commun. 1994;2281-2282.
9. Dymock B.W., Kocienski P.J., Pons J.-M. J. Chem. Soc., Chem. Commun. 1996;1053-1054.
10. (a) Yang H.W., Romo D. Tetrahedron Lett. 39:1998;2877-2880
11. (b) Romo D., Harrison P.H.M., Jenkins S.I., Riddoch R.W., Park K., Yang H.W., Zhao C., Wright G.D. Bioorg. Med. Chem. 6:1998;1255-1272.
12. (a) Nelson S.G., Peelen T.J., Wan Z. Tetrahedron Lett. 40:1999;6535-6539.
13. (b) Nelson S.G., Peelen T.J., Wan Z. Tetrahedron Lett. 40:1999;6541-6543.
14. (c) Nelson S.G., Peelen T.J., Wan Z. J. Am. Chem. Soc. 121:1999;9742-9743.
15. (d) Nelson S.G., Kim B.-K., Peelen T.J. J. Am. Chem. Soc. 122:2000;9318-9319.
16. (e) Wan Z., Nelson S.G. J. Am. Chem. Soc. 122:2000;10470-10471.
17. (f) Nelson S.G., Spencer K.L. Angew. Chem. Int. Ed. 39:2000;1323-1325
18. (g) Zipp G.G., Hilifiker M.A., Nelson S.G. Org. Lett. 4:2002;1823-1826.
19. (a) Borrmann D., Wegler R. Chem. Ber. 99:1966;1245.
20. (b) Borrmann D., Wegler R. Chem. Ber. 100:1967;1575.
21. Wynberg H., Staring E.G. J. Org. Chem. 50:1985;1977-1979.
22. (a) Tennyson R., Romo D. J. Org. Chem., 65:2000;7248-7252.
23. (b) Yang H.W., Zhao C., Romo D. Tetrahedron. 53:1997;16471-16488.
24. (c) Cortez G.S., Oh S.H., Romo D. Synthesis. 2001;1731-1736.
25. (d) Cortez G.S., Tennyson R.L., Romo D. J. Am. Chem. Soc. 123:2001;7945-7946.
26. (a) Calter M.A. J. Org. Chem. 61:1996;8006-8007.
27. (b) Calter M.A., Guo X. J. Org. Chem. 63:1998;5308-5309
28. (c) Calter M.A., Liao W. J. Am. Chem. Soc. 124:2002;13127-13129.
29. (a) Evans D.A., Sjogren E.B. Tetrahedron Lett. 26:1985;3783-3786.
30. (b) Matsui S., Hashimoto Y., Saigo K. Synthesis. 1998;1161-1166
31. (c) Saul R., Kopf J., Köll P. Tetrahedron: Asymmetry. 2000;423-433.
32. Hegedus L.S. Acc. Chem. Res. 28:1995;299-305.
33. Baldoli C., Del Buttero P., Licandro E., Maiorana S., Papagni A. Tetrahedron: Asymmetry. 5:1994;809-812.
34. Costa M.F., da Costa M.R.G., Curto M.J.M., Magrinho M., Damas A.M., Gales L. J. Organomet. Chem. 2001;27-40.
35. (a) Ferraris D., Young B., Cox C., Drury W.J. III, Dudding T., Lectka T. J. Org. Chem. 63:1998;6090-6091.
36. (b) Ferraris D., Young B., Dudding T., Drury W.J. III, Lectka T. Tetrahedron. 55:1999;8869-8882.
37. (c) Wack H., Drury W.J. III, Taggi A.E., Ferraris D., Lectka T. Org. Lett. 1:1999;1985-1988.
38. (d) Taggi A.E., Hafez A.M., Wack H., Young B., Drury W.J. III, Leckta T. J. Am. Chem. Soc. 122:2000;7831-7832.
39. (e) Hafez A.M., Taggi A.E., Wack H., Drury W.J. III, Leckta T. Org. Lett. 2:2000;3963-3965.
40. (f) Hafez A.M., Taggi A.E., Dudding T., Leckta T. J. Am. Chem. Soc. 123:2001;10853-10859.
41. (g) Dudding T., Hafez A.M., Taggi A.E., Wagerle T.R., Leckta T. Org. Lett. 3:2002;387-390.
42. (h) Taggi A.E., Wack H., Hafez A.M., France S., Leckta T. Org. Lett. 4:2002;627-629.
43. (i) France S., Wack H., Hafez A.M., Taggi A.E., Witsil D.R., Leckta T. Org. Lett. 4:2002;1603-1605.
44. (j) Taggi A.E., Hafez A.M., Wack H., Young B., Ferraris D., Leckta T. J. Am. Chem. Soc. 124:2002;6626-6635.
45. Hodous B.L., Fu G.C. J. Am. Chem. Soc. 124:2002;1578-1579.
46. (a) Nubbemeyer U. J. Org. Chem. 61:1996;3677-3686.
47. (b) Nubbemeyer U., Sudau A. Angew. Chem. Int. Ed. 37:1998;1140-1143.
48. (c) Laabs S., Scherrmann A., Sudau A., Diederich M., Kierig C., Nubbemeyer U. Synlett. 1999;25-28.
49. (d) Sudau A., Münch W., Nubbemeyer U. J. Org. Chem. 65:2000;1710-1720.
50. (e) Zhang N., Nubbemeyer U. Synthesis. 2002;242-252
51. (f) Laabs S., Münch W., Bats J.W., Nubbemeyer U. Tetrahedron. 58:2002;1317-1334.
52. (a) Yoon T.P., Dong V.M., MacMillan D.W.C. J. Am. Chem. Soc. 121:1999;9726.
53. (b) Dong V.M., MacMillan D.W.C. J. Am. Chem. Soc. 123:2001;2448-2449.
54. (c) Yoon T.P., MacMillan D.W.C. J. Am. Chem. Soc. 123:2001;2911-2912.
55. (a) Larsen R.D., Corley E.G., Davis P., Reider P.J., Grabowski E.J.J. J. Am. Chem. Soc. 111:1989;7650-7651.
56. (b) Senanayake C.H., Larsen R.D., Bill T.J., Liu J., Corley E.G., Reider P.J. Synlett. 1994;199-200.
57. (c) Cannizzaro C.E., Strassner T., Houk K.N. J. Am. Chem. Soc. 123:2001;2668-2669.
58. (a) Pracejus H. Justus Liebigs Ann. Chem. 634:1960;9-22.
59. (b) Pracejus H., Kohi G. Justus Liebigs Ann. Chem. 722:1969;1-11.
60. (c) Pracejus H., Tille A. Chem. Ber. 96:1963;854-856.
61. (d) Pracejus H., Mätje H. J. Prakt. Chem. 24:1964;195-205.
62. Blake A.J., Friend C.L., Outram R.J., Simpkins N.S., Whitehead A.J. Tetrahedron Lett. 42:2001;2877-2881.
63. Hodous B.L., Ruble J.C., Fu G.C. J. Am. Chem. Soc. 121:1999;2637-2638.
64. (a) Durst T., Koh K. Tetrahedron Lett. 33:1992;6799-6802.
65. (b) Koh K., Ben R.N., Durst T. Tetrahedron Lett. 34:1993;4473-4476.
66. Wack H., Taggi A.E., Hafez A.M., Drury W.J. III, Leckta T. J. Am. Chem. Soc. 123:2001;1531-1532.
67. (a) Greene A.E., Charbonnier F., Luche M.-J., Moyano A. J. Am. Chem. Soc. 109:1987;4752-4753.
68. (b) de Azevedo M.B.M., Murta M.M., Greene A.E. J. Org. Chem. 57:1992;4567-4569.
69. Miranda P.C.M.L., Correia C.R.D. Tetrahedron Lett. 40:1999;7735-7738.
70. Sugimura T., Tei T., Mori A., Okuyama T., Tai A. J. Am. Chem. Soc. 122:2000;2128-2129.