Tributylphosphine-catalyzed ring-opening reaction of epoxides and aziridines with acetic anhydride

Tetrahedron Letters

Volumn 44, Issue 23, 2003, Pages 4411-4413

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

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ANHYDRIDE; AMINOALCOHOL; AZIRIDINE DERIVATIVE; EPOXIDE; ESTER DERIVATIVE; PHOSPHINE DERIVATIVE;

ACYLATION; ARTICLE; CATALYSIS; HYDROLYSIS; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; RING OPENING;

EID: 0038369752     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00943-2     Document Type: Article

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33. Some examples of phosphine catalyzed reactions: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544; (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822-825; (c) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394-395; (d) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819-10822; (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906-2908; (f) Zhang, C.; Lu, X. Synlett 1995, 645-646; (g) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670-5671; (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596; (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837; (j) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031-5041; (k) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876-1877; (l) Schneider, C.; Brauner, J. Eur. J. Org. Chem. 2001, 4445-4450; (m) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696-701; (n) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905; (o) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598; (p) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405; (q) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403.
34. Some examples of phosphine catalyzed reactions: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544; (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822-825; (c) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394-395; (d) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819-10822; (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906-2908; (f) Zhang, C.; Lu, X. Synlett 1995, 645-646; (g) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670-5671; (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596; (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837; (j) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031-5041; (k) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876-1877; (l) Schneider, C.; Brauner, J. Eur. J. Org. Chem. 2001, 4445-4450; (m) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696-701; (n) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905; (o) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598; (p) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405; (q) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403.
35. Some examples of phosphine catalyzed reactions: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544; (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822-825; (c) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394-395; (d) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819-10822; (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906-2908; (f) Zhang, C.; Lu, X. Synlett 1995, 645-646; (g) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670-5671; (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596; (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837; (j) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031-5041; (k) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876-1877; (l) Schneider, C.; Brauner, J. Eur. J. Org. Chem. 2001, 4445-4450; (m) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696-701; (n) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905; (o) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598; (p) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405; (q) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403.
36. Some examples of phosphine catalyzed reactions: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544; (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822-825; (c) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394-395; (d) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819-10822; (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906-2908; (f) Zhang, C.; Lu, X. Synlett 1995, 645-646; (g) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670-5671; (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596; (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837; (j) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031-5041; (k) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876-1877; (l) Schneider, C.; Brauner, J. Eur. J. Org. Chem. 2001, 4445-4450; (m) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696-701; (n) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905; (o) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598; (p) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405; (q) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403.
37. Some examples of phosphine catalyzed reactions: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544; (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822-825; (c) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394-395; (d) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819-10822; (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906-2908; (f) Zhang, C.; Lu, X. Synlett 1995, 645-646; (g) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670-5671; (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596; (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837; (j) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031-5041; (k) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876-1877; (l) Schneider, C.; Brauner, J. Eur. J. Org. Chem. 2001, 4445-4450; (m) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696-701; (n) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905; (o) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598; (p) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405; (q) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403.
38. Some examples of phosphine catalyzed reactions: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544; (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822-825; (c) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394-395; (d) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819-10822; (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906-2908; (f) Zhang, C.; Lu, X. Synlett 1995, 645-646; (g) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670-5671; (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596; (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837; (j) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031-5041; (k) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876-1877; (l) Schneider, C.; Brauner, J. Eur. J. Org. Chem. 2001, 4445-4450; (m) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696-701; (n) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905; (o) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598; (p) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405; (q) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403.
39. Some examples of phosphine catalyzed reactions: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544; (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822-825; (c) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394-395; (d) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819-10822; (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906-2908; (f) Zhang, C.; Lu, X. Synlett 1995, 645-646; (g) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670-5671; (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596; (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837; (j) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031-5041; (k) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876-1877; (l) Schneider, C.; Brauner, J. Eur. J. Org. Chem. 2001, 4445-4450; (m) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696-701; (n) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905; (o) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598; (p) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405; (q) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403.
40. Some examples of phosphine catalyzed reactions: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544; (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822-825; (c) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394-395; (d) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819-10822; (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906-2908; (f) Zhang, C.; Lu, X. Synlett 1995, 645-646; (g) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670-5671; (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596; (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837; (j) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031-5041; (k) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876-1877; (l) Schneider, C.; Brauner, J. Eur. J. Org. Chem. 2001, 4445-4450; (m) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696-701; (n) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905; (o) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598; (p) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405; (q) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403.
41. Some examples of phosphine catalyzed reactions: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544; (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822-825; (c) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394-395; (d) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819-10822; (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906-2908; (f) Zhang, C.; Lu, X. Synlett 1995, 645-646; (g) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670-5671; (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596; (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837; (j) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031-5041; (k) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876-1877; (l) Schneider, C.; Brauner, J. Eur. J. Org. Chem. 2001, 4445-4450; (m) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696-701; (n) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905; (o) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598; (p) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405; (q) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403.
42. Some examples of phosphine catalyzed reactions: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544; (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822-825; (c) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394-395; (d) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819-10822; (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906-2908; (f) Zhang, C.; Lu, X. Synlett 1995, 645-646; (g) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670-5671; (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596; (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837; (j) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031-5041; (k) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876-1877; (l) Schneider, C.; Brauner, J. Eur. J. Org. Chem. 2001, 4445-4450; (m) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696-701; (n) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905; (o) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598; (p) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405; (q) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403.
43. Some examples of phosphine catalyzed reactions: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544; (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822-825; (c) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394-395; (d) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819-10822; (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906-2908; (f) Zhang, C.; Lu, X. Synlett 1995, 645-646; (g) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670-5671; (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596; (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837; (j) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031-5041; (k) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876-1877; (l) Schneider, C.; Brauner, J. Eur. J. Org. Chem. 2001, 4445-4450; (m) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696-701; (n) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905; (o) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598; (p) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405; (q) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403.
44. Some examples of phosphine catalyzed reactions: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544; (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822-825; (c) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394-395; (d) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819-10822; (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906-2908; (f) Zhang, C.; Lu, X. Synlett 1995, 645-646; (g) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670-5671; (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596; (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837; (j) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031-5041; (k) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876-1877; (l) Schneider, C.; Brauner, J. Eur. J. Org. Chem. 2001, 4445-4450; (m) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696-701; (n) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905; (o) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598; (p) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405; (q) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403.
45. Some examples of phosphine catalyzed reactions: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544; (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822-825; (c) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394-395; (d) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819-10822; (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906-2908; (f) Zhang, C.; Lu, X. Synlett 1995, 645-646; (g) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670-5671; (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596; (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837; (j) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031-5041; (k) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876-1877; (l) Schneider, C.; Brauner, J. Eur. J. Org. Chem. 2001, 4445-4450; (m) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696-701; (n) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905; (o) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598; (p) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405; (q) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403.
46. Some examples of phosphine catalyzed reactions: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544; (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822-825; (c) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394-395; (d) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819-10822; (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906-2908; (f) Zhang, C.; Lu, X. Synlett 1995, 645-646; (g) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670-5671; (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596; (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837; (j) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031-5041; (k) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876-1877; (l) Schneider, C.; Brauner, J. Eur. J. Org. Chem. 2001, 4445-4450; (m) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696-701; (n) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905; (o) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598; (p) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405; (q) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403.
47. Some examples of phosphine catalyzed reactions: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544; (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822-825; (c) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394-395; (d) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819-10822; (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906-2908; (f) Zhang, C.; Lu, X. Synlett 1995, 645-646; (g) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670-5671; (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596; (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837; (j) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031-5041; (k) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876-1877; (l) Schneider, C.; Brauner, J. Eur. J. Org. Chem. 2001, 4445-4450; (m) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696-701; (n) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905; (o) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598; (p) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405; (q) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403.
48. Some examples of phosphine catalyzed reactions: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544; (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822-825; (c) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394-395; (d) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819-10822; (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906-2908; (f) Zhang, C.; Lu, X. Synlett 1995, 645-646; (g) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670-5671; (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596; (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837; (j) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031-5041; (k) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876-1877; (l) Schneider, C.; Brauner, J. Eur. J. Org. Chem. 2001, 4445-4450; (m) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696-701; (n) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905; (o) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598; (p) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405; (q) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403.
49. Some examples of phosphine catalyzed reactions: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544; (b) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822-825; (c) Guo, C.; Lu, X. J. Chem. Soc., Chem. Commun. 1993, 394-395; (d) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 10819-10822; (e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906-2908; (f) Zhang, C.; Lu, X. Synlett 1995, 645-646; (g) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670-5671; (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596; (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837; (j) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031-5041; (k) Shi, M.; Xu, Y. M. Chem. Commun. 2001, 1876-1877; (l) Schneider, C.; Brauner, J. Eur. J. Org. Chem. 2001, 4445-4450; (m) Shi, M.; Xu, Y. M. Eur. J. Org. Chem. 2002, 696-701; (n) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905; (o) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598; (p) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405; (q) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403.
50. Crout D.H.G., Gaudet V.S.B., Laumen K., Schneider M.P. J. Chem. Soc., Chem. Commun. 10:1986;808-810.
51. 4. Calcd: C, 57.86; H, 6.80; N, 4.50. Found: C, 58.71; H, 7.04; N, 4.08.