A direct route to C-vinylaziridines: Reaction of N-sufonylimines with allylic ylides under phase-transfer conditions or with preformed ylides at low temperature

Journal of Organic Chemistry

Volumn 61, Issue 14, 1996, Pages 4641-4648

  Li, An Hu ^a   Dai, Li Xin ^a   Hou, Xue Long ^a   Chen, Min Bo ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001330004     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952245d     Document Type: Article

References (68)

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28. For methylene group transfer: (a) Ruano, J. L. G.; Fernandez, I.; Hamdouchi, C. Tetrahedron Lett. 1995, 36, 295. (b) Mosset, P.; Grée, R. Synth. Commun. 1985, 15, 749. (c) Tewari, R. S.; Awasthi, A. K.; Awasthi, A. Synthesis 1983, 330. (d) Elmes, B. C. Tetrahedron Lett. 1971, 4139. (e) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353. (f) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 3782. (g) Franzen, V.; Driesen, H.-E. Chem. Ber. 1963, 96, 1881. (h) Hortmann, A. G.; Robertson, D. A. J. Am. Chem. Soc. 1967, 89, 5974. (i) Hortmann, A. G.; Robertson, D. A. J. Am. Chem. Soc. 1972, 94, 2758. For ethylidene group transfer: (j) Johnson, C. R.; Janiga, E. R. J. Am. Chem. Soc. 1973, 95, 7692.
29. For methylene group transfer: (a) Ruano, J. L. G.; Fernandez, I.; Hamdouchi, C. Tetrahedron Lett. 1995, 36, 295. (b) Mosset, P.; Grée, R. Synth. Commun. 1985, 15, 749. (c) Tewari, R. S.; Awasthi, A. K.; Awasthi, A. Synthesis 1983, 330. (d) Elmes, B. C. Tetrahedron Lett. 1971, 4139. (e) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353. (f) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 3782. (g) Franzen, V.; Driesen, H.-E. Chem. Ber. 1963, 96, 1881. (h) Hortmann, A. G.; Robertson, D. A. J. Am. Chem. Soc. 1967, 89, 5974. (i) Hortmann, A. G.; Robertson, D. A. J. Am. Chem. Soc. 1972, 94, 2758. For ethylidene group transfer: (j) Johnson, C. R.; Janiga, E. R. J. Am. Chem. Soc. 1973, 95, 7692.
30. For methylene group transfer: (a) Ruano, J. L. G.; Fernandez, I.; Hamdouchi, C. Tetrahedron Lett. 1995, 36, 295. (b) Mosset, P.; Grée, R. Synth. Commun. 1985, 15, 749. (c) Tewari, R. S.; Awasthi, A. K.; Awasthi, A. Synthesis 1983, 330. (d) Elmes, B. C. Tetrahedron Lett. 1971, 4139. (e) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353. (f) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 3782. (g) Franzen, V.; Driesen, H.-E. Chem. Ber. 1963, 96, 1881. (h) Hortmann, A. G.; Robertson, D. A. J. Am. Chem. Soc. 1967, 89, 5974. (i) Hortmann, A. G.; Robertson, D. A. J. Am. Chem. Soc. 1972, 94, 2758. For ethylidene group transfer: (j) Johnson, C. R.; Janiga, E. R. J. Am. Chem. Soc. 1973, 95, 7692.
31. For methylene group transfer: (a) Ruano, J. L. G.; Fernandez, I.; Hamdouchi, C. Tetrahedron Lett. 1995, 36, 295. (b) Mosset, P.; Grée, R. Synth. Commun. 1985, 15, 749. (c) Tewari, R. S.; Awasthi, A. K.; Awasthi, A. Synthesis 1983, 330. (d) Elmes, B. C. Tetrahedron Lett. 1971, 4139. (e) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353. (f) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 3782. (g) Franzen, V.; Driesen, H.-E. Chem. Ber. 1963, 96, 1881. (h) Hortmann, A. G.; Robertson, D. A. J. Am. Chem. Soc. 1967, 89, 5974. (i) Hortmann, A. G.; Robertson, D. A. J. Am. Chem. Soc. 1972, 94, 2758. For ethylidene group transfer: (j) Johnson, C. R.; Janiga, E. R. J. Am. Chem. Soc. 1973, 95, 7692.
32. For methylene group transfer: (a) Ruano, J. L. G.; Fernandez, I.; Hamdouchi, C. Tetrahedron Lett. 1995, 36, 295. (b) Mosset, P.; Grée, R. Synth. Commun. 1985, 15, 749. (c) Tewari, R. S.; Awasthi, A. K.; Awasthi, A. Synthesis 1983, 330. (d) Elmes, B. C. Tetrahedron Lett. 1971, 4139. (e) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353. (f) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 3782. (g) Franzen, V.; Driesen, H.-E. Chem. Ber. 1963, 96, 1881. (h) Hortmann, A. G.; Robertson, D. A. J. Am. Chem. Soc. 1967, 89, 5974. (i) Hortmann, A. G.; Robertson, D. A. J. Am. Chem. Soc. 1972, 94, 2758. For ethylidene group transfer: (j) Johnson, C. R.; Janiga, E. R. J. Am. Chem. Soc. 1973, 95, 7692.
33. For methylene group transfer: (a) Ruano, J. L. G.; Fernandez, I.; Hamdouchi, C. Tetrahedron Lett. 1995, 36, 295. (b) Mosset, P.; Grée, R. Synth. Commun. 1985, 15, 749. (c) Tewari, R. S.; Awasthi, A. K.; Awasthi, A. Synthesis 1983, 330. (d) Elmes, B. C. Tetrahedron Lett. 1971, 4139. (e) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353. (f) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 3782. (g) Franzen, V.; Driesen, H.-E. Chem. Ber. 1963, 96, 1881. (h) Hortmann, A. G.; Robertson, D. A. J. Am. Chem. Soc. 1967, 89, 5974. (i) Hortmann, A. G.; Robertson, D. A. J. Am. Chem. Soc. 1972, 94, 2758. For ethylidene group transfer: (j) Johnson, C. R.; Janiga, E. R. J. Am. Chem. Soc. 1973, 95, 7692.
34. For methylene group transfer: (a) Ruano, J. L. G.; Fernandez, I.; Hamdouchi, C. Tetrahedron Lett. 1995, 36, 295. (b) Mosset, P.; Grée, R. Synth. Commun. 1985, 15, 749. (c) Tewari, R. S.; Awasthi, A. K.; Awasthi, A. Synthesis 1983, 330. (d) Elmes, B. C. Tetrahedron Lett. 1971, 4139. (e) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353. (f) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 3782. (g) Franzen, V.; Driesen, H.-E. Chem. Ber. 1963, 96, 1881. (h) Hortmann, A. G.; Robertson, D. A. J. Am. Chem. Soc. 1967, 89, 5974. (i) Hortmann, A. G.; Robertson, D. A. J. Am. Chem. Soc. 1972, 94, 2758. For ethylidene group transfer: (j) Johnson, C. R.; Janiga, E. R. J. Am. Chem. Soc. 1973, 95, 7692.
35. For methylene group transfer: (a) Ruano, J. L. G.; Fernandez, I.; Hamdouchi, C. Tetrahedron Lett. 1995, 36, 295. (b) Mosset, P.; Grée, R. Synth. Commun. 1985, 15, 749. (c) Tewari, R. S.; Awasthi, A. K.; Awasthi, A. Synthesis 1983, 330. (d) Elmes, B. C. Tetrahedron Lett. 1971, 4139. (e) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353. (f) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 3782. (g) Franzen, V.; Driesen, H.-E. Chem. Ber. 1963, 96, 1881. (h) Hortmann, A. G.; Robertson, D. A. J. Am. Chem. Soc. 1967, 89, 5974. (i) Hortmann, A. G.; Robertson, D. A. J. Am. Chem. Soc. 1972, 94, 2758. For ethylidene group transfer: (j) Johnson, C. R.; Janiga, E. R. J. Am. Chem. Soc. 1973, 95, 7692.
36. For methylene group transfer: (a) Ruano, J. L. G.; Fernandez, I.; Hamdouchi, C. Tetrahedron Lett. 1995, 36, 295. (b) Mosset, P.; Grée, R. Synth. Commun. 1985, 15, 749. (c) Tewari, R. S.; Awasthi, A. K.; Awasthi, A. Synthesis 1983, 330. (d) Elmes, B. C. Tetrahedron Lett. 1971, 4139. (e) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353. (f) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 3782. (g) Franzen, V.; Driesen, H.-E. Chem. Ber. 1963, 96, 1881. (h) Hortmann, A. G.; Robertson, D. A. J. Am. Chem. Soc. 1967, 89, 5974. (i) Hortmann, A. G.; Robertson, D. A. J. Am. Chem. Soc. 1972, 94, 2758. For ethylidene group transfer: (j) Johnson, C. R.; Janiga, E. R. J. Am. Chem. Soc. 1973, 95, 7692.
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