Efficient ring-opening reaction of epoxides and aziridines promoted by tributylphosphine in water

Journal of Organic Chemistry

Volumn 68, Issue 3, 2003, Pages 726-730

  Fan, Ren Hua ^a   Hou, Xue Long ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

RING OPENING POLYMERIZATION; WATER;

ANTI-BIFUNCTIONAL PRODUCTS;

AROMATIC COMPOUNDS;

AZIRIDINE DERIVATIVE; EPOXIDE; PHOSPHINE DERIVATIVE; REAGENT; TRIBUTYLPHOSPHINE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; REACTION ANALYSIS; RING OPENING; SYNTHESIS;

EID: 0037423323     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo025983s     Document Type: Article

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33. Some other examples of phosphine-catalyzed reactions, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822. (c) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819. (d) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670. (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906. (f) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394. (g) Zhang, C.; Lu, X. Synlett 1995, 645. (h) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461. (j) Matsukawa, S.; Okano, N.; Imamoto, T. Tetrahedron Lett. 2000, 41, 103. (k) Vedejs, E.; Bennett, N. S.; Conn, L. M.; Diver, S. T.; Gingras, M.; Lin, S.; Oliver, P. A.; Peterson, M. J. J. Org. Chem. 1993, 58, 7286. (l) Hayase, T.; Shibata, T.; Soai, K.; Wakatsuki, Y. Chem. Commun. 1998, 1271. (m) Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 537. (n) Vedejs, E.; Daugulis, O.; MacKay, J. A.; Rozners, E. Synlett 2001, 1499. (o) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876. (p) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696.
34. Some other examples of phosphine-catalyzed reactions, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822. (c) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819. (d) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670. (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906. (f) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394. (g) Zhang, C.; Lu, X. Synlett 1995, 645. (h) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461. (j) Matsukawa, S.; Okano, N.; Imamoto, T. Tetrahedron Lett. 2000, 41, 103. (k) Vedejs, E.; Bennett, N. S.; Conn, L. M.; Diver, S. T.; Gingras, M.; Lin, S.; Oliver, P. A.; Peterson, M. J. J. Org. Chem. 1993, 58, 7286. (l) Hayase, T.; Shibata, T.; Soai, K.; Wakatsuki, Y. Chem. Commun. 1998, 1271. (m) Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 537. (n) Vedejs, E.; Daugulis, O.; MacKay, J. A.; Rozners, E. Synlett 2001, 1499. (o) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876. (p) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696.
35. Some other examples of phosphine-catalyzed reactions, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822. (c) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819. (d) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670. (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906. (f) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394. (g) Zhang, C.; Lu, X. Synlett 1995, 645. (h) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461. (j) Matsukawa, S.; Okano, N.; Imamoto, T. Tetrahedron Lett. 2000, 41, 103. (k) Vedejs, E.; Bennett, N. S.; Conn, L. M.; Diver, S. T.; Gingras, M.; Lin, S.; Oliver, P. A.; Peterson, M. J. J. Org. Chem. 1993, 58, 7286. (l) Hayase, T.; Shibata, T.; Soai, K.; Wakatsuki, Y. Chem. Commun. 1998, 1271. (m) Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 537. (n) Vedejs, E.; Daugulis, O.; MacKay, J. A.; Rozners, E. Synlett 2001, 1499. (o) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876. (p) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696.
36. Some other examples of phosphine-catalyzed reactions, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822. (c) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819. (d) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670. (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906. (f) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394. (g) Zhang, C.; Lu, X. Synlett 1995, 645. (h) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461. (j) Matsukawa, S.; Okano, N.; Imamoto, T. Tetrahedron Lett. 2000, 41, 103. (k) Vedejs, E.; Bennett, N. S.; Conn, L. M.; Diver, S. T.; Gingras, M.; Lin, S.; Oliver, P. A.; Peterson, M. J. J. Org. Chem. 1993, 58, 7286. (l) Hayase, T.; Shibata, T.; Soai, K.; Wakatsuki, Y. Chem. Commun. 1998, 1271. (m) Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 537. (n) Vedejs, E.; Daugulis, O.; MacKay, J. A.; Rozners, E. Synlett 2001, 1499. (o) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876. (p) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696.
37. Some other examples of phosphine-catalyzed reactions, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822. (c) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819. (d) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670. (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906. (f) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394. (g) Zhang, C.; Lu, X. Synlett 1995, 645. (h) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461. (j) Matsukawa, S.; Okano, N.; Imamoto, T. Tetrahedron Lett. 2000, 41, 103. (k) Vedejs, E.; Bennett, N. S.; Conn, L. M.; Diver, S. T.; Gingras, M.; Lin, S.; Oliver, P. A.; Peterson, M. J. J. Org. Chem. 1993, 58, 7286. (l) Hayase, T.; Shibata, T.; Soai, K.; Wakatsuki, Y. Chem. Commun. 1998, 1271. (m) Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 537. (n) Vedejs, E.; Daugulis, O.; MacKay, J. A.; Rozners, E. Synlett 2001, 1499. (o) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876. (p) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696.
38. Some other examples of phosphine-catalyzed reactions, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822. (c) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819. (d) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670. (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906. (f) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394. (g) Zhang, C.; Lu, X. Synlett 1995, 645. (h) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461. (j) Matsukawa, S.; Okano, N.; Imamoto, T. Tetrahedron Lett. 2000, 41, 103. (k) Vedejs, E.; Bennett, N. S.; Conn, L. M.; Diver, S. T.; Gingras, M.; Lin, S.; Oliver, P. A.; Peterson, M. J. J. Org. Chem. 1993, 58, 7286. (l) Hayase, T.; Shibata, T.; Soai, K.; Wakatsuki, Y. Chem. Commun. 1998, 1271. (m) Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 537. (n) Vedejs, E.; Daugulis, O.; MacKay, J. A.; Rozners, E. Synlett 2001, 1499. (o) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876. (p) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696.
39. Some other examples of phosphine-catalyzed reactions, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822. (c) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819. (d) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670. (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906. (f) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394. (g) Zhang, C.; Lu, X. Synlett 1995, 645. (h) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461. (j) Matsukawa, S.; Okano, N.; Imamoto, T. Tetrahedron Lett. 2000, 41, 103. (k) Vedejs, E.; Bennett, N. S.; Conn, L. M.; Diver, S. T.; Gingras, M.; Lin, S.; Oliver, P. A.; Peterson, M. J. J. Org. Chem. 1993, 58, 7286. (l) Hayase, T.; Shibata, T.; Soai, K.; Wakatsuki, Y. Chem. Commun. 1998, 1271. (m) Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 537. (n) Vedejs, E.; Daugulis, O.; MacKay, J. A.; Rozners, E. Synlett 2001, 1499. (o) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876. (p) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696.
40. Some other examples of phosphine-catalyzed reactions, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822. (c) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819. (d) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670. (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906. (f) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394. (g) Zhang, C.; Lu, X. Synlett 1995, 645. (h) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461. (j) Matsukawa, S.; Okano, N.; Imamoto, T. Tetrahedron Lett. 2000, 41, 103. (k) Vedejs, E.; Bennett, N. S.; Conn, L. M.; Diver, S. T.; Gingras, M.; Lin, S.; Oliver, P. A.; Peterson, M. J. J. Org. Chem. 1993, 58, 7286. (l) Hayase, T.; Shibata, T.; Soai, K.; Wakatsuki, Y. Chem. Commun. 1998, 1271. (m) Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 537. (n) Vedejs, E.; Daugulis, O.; MacKay, J. A.; Rozners, E. Synlett 2001, 1499. (o) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876. (p) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696.
41. Some other examples of phosphine-catalyzed reactions, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822. (c) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819. (d) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670. (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906. (f) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394. (g) Zhang, C.; Lu, X. Synlett 1995, 645. (h) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461. (j) Matsukawa, S.; Okano, N.; Imamoto, T. Tetrahedron Lett. 2000, 41, 103. (k) Vedejs, E.; Bennett, N. S.; Conn, L. M.; Diver, S. T.; Gingras, M.; Lin, S.; Oliver, P. A.; Peterson, M. J. J. Org. Chem. 1993, 58, 7286. (l) Hayase, T.; Shibata, T.; Soai, K.; Wakatsuki, Y. Chem. Commun. 1998, 1271. (m) Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 537. (n) Vedejs, E.; Daugulis, O.; MacKay, J. A.; Rozners, E. Synlett 2001, 1499. (o) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876. (p) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696.
42. Some other examples of phosphine-catalyzed reactions, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822. (c) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819. (d) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670. (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906. (f) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394. (g) Zhang, C.; Lu, X. Synlett 1995, 645. (h) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461. (j) Matsukawa, S.; Okano, N.; Imamoto, T. Tetrahedron Lett. 2000, 41, 103. (k) Vedejs, E.; Bennett, N. S.; Conn, L. M.; Diver, S. T.; Gingras, M.; Lin, S.; Oliver, P. A.; Peterson, M. J. J. Org. Chem. 1993, 58, 7286. (l) Hayase, T.; Shibata, T.; Soai, K.; Wakatsuki, Y. Chem. Commun. 1998, 1271. (m) Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 537. (n) Vedejs, E.; Daugulis, O.; MacKay, J. A.; Rozners, E. Synlett 2001, 1499. (o) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876. (p) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696.
43. Some other examples of phosphine-catalyzed reactions, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822. (c) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819. (d) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670. (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906. (f) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394. (g) Zhang, C.; Lu, X. Synlett 1995, 645. (h) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461. (j) Matsukawa, S.; Okano, N.; Imamoto, T. Tetrahedron Lett. 2000, 41, 103. (k) Vedejs, E.; Bennett, N. S.; Conn, L. M.; Diver, S. T.; Gingras, M.; Lin, S.; Oliver, P. A.; Peterson, M. J. J. Org. Chem. 1993, 58, 7286. (l) Hayase, T.; Shibata, T.; Soai, K.; Wakatsuki, Y. Chem. Commun. 1998, 1271. (m) Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 537. (n) Vedejs, E.; Daugulis, O.; MacKay, J. A.; Rozners, E. Synlett 2001, 1499. (o) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876. (p) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696.
44. Some other examples of phosphine-catalyzed reactions, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822. (c) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819. (d) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670. (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906. (f) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394. (g) Zhang, C.; Lu, X. Synlett 1995, 645. (h) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461. (j) Matsukawa, S.; Okano, N.; Imamoto, T. Tetrahedron Lett. 2000, 41, 103. (k) Vedejs, E.; Bennett, N. S.; Conn, L. M.; Diver, S. T.; Gingras, M.; Lin, S.; Oliver, P. A.; Peterson, M. J. J. Org. Chem. 1993, 58, 7286. (l) Hayase, T.; Shibata, T.; Soai, K.; Wakatsuki, Y. Chem. Commun. 1998, 1271. (m) Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 537. (n) Vedejs, E.; Daugulis, O.; MacKay, J. A.; Rozners, E. Synlett 2001, 1499. (o) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876. (p) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696.
45. Some other examples of phosphine-catalyzed reactions, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 and references therein. (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822. (c) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819. (d) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670. (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906. (f) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394. (g) Zhang, C.; Lu, X. Synlett 1995, 645. (h) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461. (j) Matsukawa, S.; Okano, N.; Imamoto, T. Tetrahedron Lett. 2000, 41, 103. (k) Vedejs, E.; Bennett, N. S.; Conn, L. M.; Diver, S. T.; Gingras, M.; Lin, S.; Oliver, P. A.; Peterson, M. J. J. Org. Chem. 1993, 58, 7286. (l) Hayase, T.; Shibata, T.; Soai, K.; Wakatsuki, Y. Chem. Commun. 1998, 1271. (m) Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 537. (n) Vedejs, E.; Daugulis, O.; MacKay, J. A.; Rozners, E. Synlett 2001, 1499. (o) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876. (p) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696.
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