Catalytic construction and reconstruction of guanidines: Ti-mediated guanylation of amines and transamination of guanidines

Journal of the American Chemical Society

Volumn 125, Issue 27, 2003, Pages 8100-8101

  Ong, Tiow Gan ^a   Yap, Glenn P A ^a   Richeson, Darrin S ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CYANAMIDE; GUANIDINE DERIVATIVE; REAGENT; TITANIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTALLIZATION; GAS CHROMATOGRAPHY; ISOMER; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; SYNTHESIS; TEMPERATURE; TRANSAMINATION; X RAY CRYSTALLOGRAPHY;

AMINES; CATALYSIS; GUANIDINES; ORGANOMETALLIC COMPOUNDS; TITANIUM;

EID: 0038682672     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035716j     Document Type: Article

References (43)

1. For recent group 4-mediated hydroamination reactions see: (a) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935. (b) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801. (c) Doye, S.; Sibeneicher, H. Eur. J. Org. Chem. 2002, 1213. (d) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961. (e) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305. (f) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389. (g) Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880. (h) Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853. (i) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967. (j) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475. (k) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632. (l) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923. (m) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708. (n) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753. (o) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839. (p) Tillack, A.; Castro, I. G.; Hartung, C. G.; Beller, M. Angew: Chem., Int. Ed. 2002, 41, 2541. (q) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (r) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459. (s) Fairfax, D.; Stein, M.; Livinghouse, T.; Jensen, M. Organometallics 1997, 16, 1523.
2. For recent group 4-mediated hydroamination reactions see: (a) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935. (b) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801. (c) Doye, S.; Sibeneicher, H. Eur. J. Org. Chem. 2002, 1213. (d) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961. (e) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305. (f) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389. (g) Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880. (h) Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853. (i) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967. (j) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475. (k) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632. (l) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923. (m) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708. (n) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753. (o) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839. (p) Tillack, A.; Castro, I. G.; Hartung, C. G.; Beller, M. Angew: Chem., Int. Ed. 2002, 41, 2541. (q) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (r) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459. (s) Fairfax, D.; Stein, M.; Livinghouse, T.; Jensen, M. Organometallics 1997, 16, 1523.
3. For recent group 4-mediated hydroamination reactions see: (a) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935. (b) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801. (c) Doye, S.; Sibeneicher, H. Eur. J. Org. Chem. 2002, 1213. (d) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961. (e) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305. (f) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389. (g) Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880. (h) Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853. (i) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967. (j) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475. (k) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632. (l) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923. (m) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708. (n) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753. (o) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839. (p) Tillack, A.; Castro, I. G.; Hartung, C. G.; Beller, M. Angew: Chem., Int. Ed. 2002, 41, 2541. (q) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (r) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459. (s) Fairfax, D.; Stein, M.; Livinghouse, T.; Jensen, M. Organometallics 1997, 16, 1523.
4. For recent group 4-mediated hydroamination reactions see: (a) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935. (b) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801. (c) Doye, S.; Sibeneicher, H. Eur. J. Org. Chem. 2002, 1213. (d) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961. (e) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305. (f) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389. (g) Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880. (h) Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853. (i) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967. (j) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475. (k) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632. (l) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923. (m) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708. (n) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753. (o) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839. (p) Tillack, A.; Castro, I. G.; Hartung, C. G.; Beller, M. Angew: Chem., Int. Ed. 2002, 41, 2541. (q) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (r) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459. (s) Fairfax, D.; Stein, M.; Livinghouse, T.; Jensen, M. Organometallics 1997, 16, 1523.
5. For recent group 4-mediated hydroamination reactions see: (a) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935. (b) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801. (c) Doye, S.; Sibeneicher, H. Eur. J. Org. Chem. 2002, 1213. (d) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961. (e) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305. (f) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389. (g) Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880. (h) Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853. (i) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967. (j) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475. (k) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632. (l) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923. (m) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708. (n) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753. (o) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839. (p) Tillack, A.; Castro, I. G.; Hartung, C. G.; Beller, M. Angew: Chem., Int. Ed. 2002, 41, 2541. (q) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (r) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459. (s) Fairfax, D.; Stein, M.; Livinghouse, T.; Jensen, M. Organometallics 1997, 16, 1523.
6. For recent group 4-mediated hydroamination reactions see: (a) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935. (b) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801. (c) Doye, S.; Sibeneicher, H. Eur. J. Org. Chem. 2002, 1213. (d) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961. (e) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305. (f) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389. (g) Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880. (h) Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853. (i) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967. (j) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475. (k) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632. (l) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923. (m) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708. (n) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753. (o) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839. (p) Tillack, A.; Castro, I. G.; Hartung, C. G.; Beller, M. Angew: Chem., Int. Ed. 2002, 41, 2541. (q) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (r) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459. (s) Fairfax, D.; Stein, M.; Livinghouse, T.; Jensen, M. Organometallics 1997, 16, 1523.
7. For recent group 4-mediated hydroamination reactions see: (a) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935. (b) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801. (c) Doye, S.; Sibeneicher, H. Eur. J. Org. Chem. 2002, 1213. (d) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961. (e) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305. (f) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389. (g) Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880. (h) Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853. (i) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967. (j) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475. (k) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632. (l) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923. (m) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708. (n) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753. (o) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839. (p) Tillack, A.; Castro, I. G.; Hartung, C. G.; Beller, M. Angew: Chem., Int. Ed. 2002, 41, 2541. (q) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (r) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459. (s) Fairfax, D.; Stein, M.; Livinghouse, T.; Jensen, M. Organometallics 1997, 16, 1523.
8. For recent group 4-mediated hydroamination reactions see: (a) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935. (b) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801. (c) Doye, S.; Sibeneicher, H. Eur. J. Org. Chem. 2002, 1213. (d) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961. (e) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305. (f) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389. (g) Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880. (h) Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853. (i) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967. (j) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475. (k) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632. (l) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923. (m) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708. (n) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753. (o) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839. (p) Tillack, A.; Castro, I. G.; Hartung, C. G.; Beller, M. Angew: Chem., Int. Ed. 2002, 41, 2541. (q) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (r) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459. (s) Fairfax, D.; Stein, M.; Livinghouse, T.; Jensen, M. Organometallics 1997, 16, 1523.
9. For recent group 4-mediated hydroamination reactions see: (a) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935. (b) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801. (c) Doye, S.; Sibeneicher, H. Eur. J. Org. Chem. 2002, 1213. (d) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961. (e) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305. (f) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389. (g) Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880. (h) Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853. (i) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967. (j) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475. (k) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632. (l) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923. (m) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708. (n) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753. (o) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839. (p) Tillack, A.; Castro, I. G.; Hartung, C. G.; Beller, M. Angew: Chem., Int. Ed. 2002, 41, 2541. (q) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (r) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459. (s) Fairfax, D.; Stein, M.; Livinghouse, T.; Jensen, M. Organometallics 1997, 16, 1523.
10. For recent group 4-mediated hydroamination reactions see: (a) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935. (b) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801. (c) Doye, S.; Sibeneicher, H. Eur. J. Org. Chem. 2002, 1213. (d) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961. (e) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305. (f) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389. (g) Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880. (h) Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853. (i) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967. (j) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475. (k) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632. (l) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923. (m) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708. (n) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753. (o) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839. (p) Tillack, A.; Castro, I. G.; Hartung, C. G.; Beller, M. Angew: Chem., Int. Ed. 2002, 41, 2541. (q) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (r) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459. (s) Fairfax, D.; Stein, M.; Livinghouse, T.; Jensen, M. Organometallics 1997, 16, 1523.
11. For recent group 4-mediated hydroamination reactions see: (a) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935. (b) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801. (c) Doye, S.; Sibeneicher, H. Eur. J. Org. Chem. 2002, 1213. (d) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961. (e) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305. (f) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389. (g) Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880. (h) Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853. (i) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967. (j) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475. (k) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632. (l) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923. (m) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708. (n) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753. (o) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839. (p) Tillack, A.; Castro, I. G.; Hartung, C. G.; Beller, M. Angew: Chem., Int. Ed. 2002, 41, 2541. (q) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (r) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459. (s) Fairfax, D.; Stein, M.; Livinghouse, T.; Jensen, M. Organometallics 1997, 16, 1523.
12. For recent group 4-mediated hydroamination reactions see: (a) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935. (b) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801. (c) Doye, S.; Sibeneicher, H. Eur. J. Org. Chem. 2002, 1213. (d) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961. (e) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305. (f) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389. (g) Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880. (h) Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853. (i) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967. (j) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475. (k) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632. (l) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923. (m) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708. (n) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753. (o) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839. (p) Tillack, A.; Castro, I. G.; Hartung, C. G.; Beller, M. Angew: Chem., Int. Ed. 2002, 41, 2541. (q) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (r) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459. (s) Fairfax, D.; Stein, M.; Livinghouse, T.; Jensen, M. Organometallics 1997, 16, 1523.
13. For recent group 4-mediated hydroamination reactions see: (a) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935. (b) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801. (c) Doye, S.; Sibeneicher, H. Eur. J. Org. Chem. 2002, 1213. (d) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961. (e) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305. (f) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389. (g) Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880. (h) Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853. (i) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967. (j) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475. (k) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632. (l) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923. (m) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708. (n) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753. (o) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839. (p) Tillack, A.; Castro, I. G.; Hartung, C. G.; Beller, M. Angew: Chem., Int. Ed. 2002, 41, 2541. (q) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (r) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459. (s) Fairfax, D.; Stein, M.; Livinghouse, T.; Jensen, M. Organometallics 1997, 16, 1523.
14. For recent group 4-mediated hydroamination reactions see: (a) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935. (b) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801. (c) Doye, S.; Sibeneicher, H. Eur. J. Org. Chem. 2002, 1213. (d) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961. (e) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305. (f) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389. (g) Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880. (h) Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853. (i) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967. (j) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475. (k) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632. (l) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923. (m) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708. (n) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753. (o) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839. (p) Tillack, A.; Castro, I. G.; Hartung, C. G.; Beller, M. Angew: Chem., Int. Ed. 2002, 41, 2541. (q) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (r) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459. (s) Fairfax, D.; Stein, M.; Livinghouse, T.; Jensen, M. Organometallics 1997, 16, 1523.
15. For recent group 4-mediated hydroamination reactions see: (a) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935. (b) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801. (c) Doye, S.; Sibeneicher, H. Eur. J. Org. Chem. 2002, 1213. (d) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961. (e) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305. (f) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389. (g) Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880. (h) Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853. (i) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967. (j) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475. (k) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632. (l) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923. (m) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708. (n) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753. (o) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839. (p) Tillack, A.; Castro, I. G.; Hartung, C. G.; Beller, M. Angew: Chem., Int. Ed. 2002, 41, 2541. (q) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (r) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459. (s) Fairfax, D.; Stein, M.; Livinghouse, T.; Jensen, M. Organometallics 1997, 16, 1523.
16. For recent group 4-mediated hydroamination reactions see: (a) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935. (b) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801. (c) Doye, S.; Sibeneicher, H. Eur. J. Org. Chem. 2002, 1213. (d) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961. (e) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305. (f) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389. (g) Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880. (h) Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853. (i) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967. (j) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475. (k) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632. (l) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923. (m) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708. (n) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753. (o) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839. (p) Tillack, A.; Castro, I. G.; Hartung, C. G.; Beller, M. Angew: Chem., Int. Ed. 2002, 41, 2541. (q) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (r) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459. (s) Fairfax, D.; Stein, M.; Livinghouse, T.; Jensen, M. Organometallics 1997, 16, 1523.
17. For recent group 4-mediated hydroamination reactions see: (a) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935. (b) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801. (c) Doye, S.; Sibeneicher, H. Eur. J. Org. Chem. 2002, 1213. (d) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961. (e) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305. (f) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389. (g) Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880. (h) Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853. (i) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967. (j) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475. (k) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632. (l) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923. (m) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708. (n) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753. (o) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839. (p) Tillack, A.; Castro, I. G.; Hartung, C. G.; Beller, M. Angew: Chem., Int. Ed. 2002, 41, 2541. (q) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (r) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459. (s) Fairfax, D.; Stein, M.; Livinghouse, T.; Jensen, M. Organometallics 1997, 16, 1523.
18. For recent group 4-mediated hydroamination reactions see: (a) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935. (b) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801. (c) Doye, S.; Sibeneicher, H. Eur. J. Org. Chem. 2002, 1213. (d) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961. (e) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305. (f) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389. (g) Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880. (h) Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853. (i) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967. (j) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475. (k) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632. (l) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923. (m) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708. (n) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753. (o) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839. (p) Tillack, A.; Castro, I. G.; Hartung, C. G.; Beller, M. Angew: Chem., Int. Ed. 2002, 41, 2541. (q) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (r) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459. (s) Fairfax, D.; Stein, M.; Livinghouse, T.; Jensen, M. Organometallics 1997, 16, 1523.
19. For recent group 4-mediated hydroamination reactions see: (a) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935. (b) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801. (c) Doye, S.; Sibeneicher, H. Eur. J. Org. Chem. 2002, 1213. (d) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961. (e) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305. (f) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389. (g) Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880. (h) Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853. (i) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967. (j) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475. (k) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632. (l) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923. (m) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708. (n) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753. (o) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839. (p) Tillack, A.; Castro, I. G.; Hartung, C. G.; Beller, M. Angew: Chem., Int. Ed. 2002, 41, 2541. (q) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (r) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459. (s) Fairfax, D.; Stein, M.; Livinghouse, T.; Jensen, M. Organometallics 1997, 16, 1523.
20. (a) Zuckerman, R. L.; Bergman, R. G. Organometallics 2001, 20, 1792.
21. (b) Zuckerman, R. L.; Krska, S. W.; Bergman, R. G. J. Am. Chem. Soc. 2000, 122, 751.
22. (c) Zuckerman, R. L.; Bergman, R. G. Organometallics 2000, 19, 4795.
23. (d) Krska, S. W.; Zuckerman, R. L.; Bergman, R. G. J. Am. Chem. Soc. 1890, 12, 11828.
24. (e) Meyer, K. E.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc, 1994, 116, 2669.
25. Elred, S. E.; Stone, D. A.; Gellman, S. H.; Stahl, S. S. J. Am. Chem. Soc. 2003, 125, 3422.
26. Structure and preparation of 1b are providcd in Supporting Information.
27. (a) Guanidines: Historical, Biological, Biochemical and Clinical Aspects of the Naturally Occurring Guanidino Compounds; Mori, A., Cohen, B. D., Lowenthal, A., Eds.; Plenum Press: New York, 1985.
28. Guandines 2: Further Explorations of the Biological and Clinical Significance of Guanidino Compounds: Mori, A., Cohen, B. D., Koide, H., Eds.; Plenum Press: New York, 1987.
29. For recent examples of amine guanylations employing various reagents see: (a) Yu, Y.; Ostresh, J. M.; Houghten, R. A. J. Org. Chem. 2002, 67, 3138. (b) Linton, B. R.; Carr, A. J.; Orner, B. P.; Hamilton, A. D. J. Org. Chem. 2000, 65, 1566. (c) Tamaki, M.; Han, G.; Hruby, V. J. J. Org. Chem. 2001, 66, 1038. (d) Feichtinger, K.; Zapf, C.; Sings, H. L.; Goodman, M. J. Org. Chem. 1998, 63, 3804. (e) Ghosh, A. K.; Hol, W. G. J.; Fan, E. J. Org. Chem. 2001, 66, 2161. (f) Wu, Y.-Q.; Hamilton, S. K.; Wilkinson, D. E.; Hamilton, G. S. J. Org. Chem. 2002, 67, 7553. (g) Musiol, H.-J.; Moroder, L. Org. Lett. 2001, 3, 3859. (h) Katritzky, A. R.; Rogovoy, B. V.; Chassaing, C.; Vvedensky, V. J. Org. Chem. 2000, 65, 8080. (i) Ramadas, K.; Srinivasan, N. Tetrahedron Lett. 1995, 36, 2841. (j) Kent, D. R.; Cody, W. L.; Doherty, A. M. Tetrahedron Lett. 1996, 37, 8711.
30. For recent examples of amine guanylations employing various reagents see: (a) Yu, Y.; Ostresh, J. M.; Houghten, R. A. J. Org. Chem. 2002, 67, 3138. (b) Linton, B. R.; Carr, A. J.; Orner, B. P.; Hamilton, A. D. J. Org. Chem. 2000, 65, 1566. (c) Tamaki, M.; Han, G.; Hruby, V. J. J. Org. Chem. 2001, 66, 1038. (d) Feichtinger, K.; Zapf, C.; Sings, H. L.; Goodman, M. J. Org. Chem. 1998, 63, 3804. (e) Ghosh, A. K.; Hol, W. G. J.; Fan, E. J. Org. Chem. 2001, 66, 2161. (f) Wu, Y.-Q.; Hamilton, S. K.; Wilkinson, D. E.; Hamilton, G. S. J. Org. Chem. 2002, 67, 7553. (g) Musiol, H.-J.; Moroder, L. Org. Lett. 2001, 3, 3859. (h) Katritzky, A. R.; Rogovoy, B. V.; Chassaing, C.; Vvedensky, V. J. Org. Chem. 2000, 65, 8080. (i) Ramadas, K.; Srinivasan, N. Tetrahedron Lett. 1995, 36, 2841. (j) Kent, D. R.; Cody, W. L.; Doherty, A. M. Tetrahedron Lett. 1996, 37, 8711.
31. For recent examples of amine guanylations employing various reagents see: (a) Yu, Y.; Ostresh, J. M.; Houghten, R. A. J. Org. Chem. 2002, 67, 3138. (b) Linton, B. R.; Carr, A. J.; Orner, B. P.; Hamilton, A. D. J. Org. Chem. 2000, 65, 1566. (c) Tamaki, M.; Han, G.; Hruby, V. J. J. Org. Chem. 2001, 66, 1038. (d) Feichtinger, K.; Zapf, C.; Sings, H. L.; Goodman, M. J. Org. Chem. 1998, 63, 3804. (e) Ghosh, A. K.; Hol, W. G. J.; Fan, E. J. Org. Chem. 2001, 66, 2161. (f) Wu, Y.-Q.; Hamilton, S. K.; Wilkinson, D. E.; Hamilton, G. S. J. Org. Chem. 2002, 67, 7553. (g) Musiol, H.-J.; Moroder, L. Org. Lett. 2001, 3, 3859. (h) Katritzky, A. R.; Rogovoy, B. V.; Chassaing, C.; Vvedensky, V. J. Org. Chem. 2000, 65, 8080. (i) Ramadas, K.; Srinivasan, N. Tetrahedron Lett. 1995, 36, 2841. (j) Kent, D. R.; Cody, W. L.; Doherty, A. M. Tetrahedron Lett. 1996, 37, 8711.
32. For recent examples of amine guanylations employing various reagents see: (a) Yu, Y.; Ostresh, J. M.; Houghten, R. A. J. Org. Chem. 2002, 67, 3138. (b) Linton, B. R.; Carr, A. J.; Orner, B. P.; Hamilton, A. D. J. Org. Chem. 2000, 65, 1566. (c) Tamaki, M.; Han, G.; Hruby, V. J. J. Org. Chem. 2001, 66, 1038. (d) Feichtinger, K.; Zapf, C.; Sings, H. L.; Goodman, M. J. Org. Chem. 1998, 63, 3804. (e) Ghosh, A. K.; Hol, W. G. J.; Fan, E. J. Org. Chem. 2001, 66, 2161. (f) Wu, Y.-Q.; Hamilton, S. K.; Wilkinson, D. E.; Hamilton, G. S. J. Org. Chem. 2002, 67, 7553. (g) Musiol, H.-J.; Moroder, L. Org. Lett. 2001, 3, 3859. (h) Katritzky, A. R.; Rogovoy, B. V.; Chassaing, C.; Vvedensky, V. J. Org. Chem. 2000, 65, 8080. (i) Ramadas, K.; Srinivasan, N. Tetrahedron Lett. 1995, 36, 2841. (j) Kent, D. R.; Cody, W. L.; Doherty, A. M. Tetrahedron Lett. 1996, 37, 8711.
33. For recent examples of amine guanylations employing various reagents see: (a) Yu, Y.; Ostresh, J. M.; Houghten, R. A. J. Org. Chem. 2002, 67, 3138. (b) Linton, B. R.; Carr, A. J.; Orner, B. P.; Hamilton, A. D. J. Org. Chem. 2000, 65, 1566. (c) Tamaki, M.; Han, G.; Hruby, V. J. J. Org. Chem. 2001, 66, 1038. (d) Feichtinger, K.; Zapf, C.; Sings, H. L.; Goodman, M. J. Org. Chem. 1998, 63, 3804. (e) Ghosh, A. K.; Hol, W. G. J.; Fan, E. J. Org. Chem. 2001, 66, 2161. (f) Wu, Y.-Q.; Hamilton, S. K.; Wilkinson, D. E.; Hamilton, G. S. J. Org. Chem. 2002, 67, 7553. (g) Musiol, H.-J.; Moroder, L. Org. Lett. 2001, 3, 3859. (h) Katritzky, A. R.; Rogovoy, B. V.; Chassaing, C.; Vvedensky, V. J. Org. Chem. 2000, 65, 8080. (i) Ramadas, K.; Srinivasan, N. Tetrahedron Lett. 1995, 36, 2841. (j) Kent, D. R.; Cody, W. L.; Doherty, A. M. Tetrahedron Lett. 1996, 37, 8711.
34. For recent examples of amine guanylations employing various reagents see: (a) Yu, Y.; Ostresh, J. M.; Houghten, R. A. J. Org. Chem. 2002, 67, 3138. (b) Linton, B. R.; Carr, A. J.; Orner, B. P.; Hamilton, A. D. J. Org. Chem. 2000, 65, 1566. (c) Tamaki, M.; Han, G.; Hruby, V. J. J. Org. Chem. 2001, 66, 1038. (d) Feichtinger, K.; Zapf, C.; Sings, H. L.; Goodman, M. J. Org. Chem. 1998, 63, 3804. (e) Ghosh, A. K.; Hol, W. G. J.; Fan, E. J. Org. Chem. 2001, 66, 2161. (f) Wu, Y.-Q.; Hamilton, S. K.; Wilkinson, D. E.; Hamilton, G. S. J. Org. Chem. 2002, 67, 7553. (g) Musiol, H.-J.; Moroder, L. Org. Lett. 2001, 3, 3859. (h) Katritzky, A. R.; Rogovoy, B. V.; Chassaing, C.; Vvedensky, V. J. Org. Chem. 2000, 65, 8080. (i) Ramadas, K.; Srinivasan, N. Tetrahedron Lett. 1995, 36, 2841. (j) Kent, D. R.; Cody, W. L.; Doherty, A. M. Tetrahedron Lett. 1996, 37, 8711.
35. For recent examples of amine guanylations employing various reagents see: (a) Yu, Y.; Ostresh, J. M.; Houghten, R. A. J. Org. Chem. 2002, 67, 3138. (b) Linton, B. R.; Carr, A. J.; Orner, B. P.; Hamilton, A. D. J. Org. Chem. 2000, 65, 1566. (c) Tamaki, M.; Han, G.; Hruby, V. J. J. Org. Chem. 2001, 66, 1038. (d) Feichtinger, K.; Zapf, C.; Sings, H. L.; Goodman, M. J. Org. Chem. 1998, 63, 3804. (e) Ghosh, A. K.; Hol, W. G. J.; Fan, E. J. Org. Chem. 2001, 66, 2161. (f) Wu, Y.-Q.; Hamilton, S. K.; Wilkinson, D. E.; Hamilton, G. S. J. Org. Chem. 2002, 67, 7553. (g) Musiol, H.-J.; Moroder, L. Org. Lett. 2001, 3, 3859. (h) Katritzky, A. R.; Rogovoy, B. V.; Chassaing, C.; Vvedensky, V. J. Org. Chem. 2000, 65, 8080. (i) Ramadas, K.; Srinivasan, N. Tetrahedron Lett. 1995, 36, 2841. (j) Kent, D. R.; Cody, W. L.; Doherty, A. M. Tetrahedron Lett. 1996, 37, 8711.
36. For recent examples of amine guanylations employing various reagents see: (a) Yu, Y.; Ostresh, J. M.; Houghten, R. A. J. Org. Chem. 2002, 67, 3138. (b) Linton, B. R.; Carr, A. J.; Orner, B. P.; Hamilton, A. D. J. Org. Chem. 2000, 65, 1566. (c) Tamaki, M.; Han, G.; Hruby, V. J. J. Org. Chem. 2001, 66, 1038. (d) Feichtinger, K.; Zapf, C.; Sings, H. L.; Goodman, M. J. Org. Chem. 1998, 63, 3804. (e) Ghosh, A. K.; Hol, W. G. J.; Fan, E. J. Org. Chem. 2001, 66, 2161. (f) Wu, Y.-Q.; Hamilton, S. K.; Wilkinson, D. E.; Hamilton, G. S. J. Org. Chem. 2002, 67, 7553. (g) Musiol, H.-J.; Moroder, L. Org. Lett. 2001, 3, 3859. (h) Katritzky, A. R.; Rogovoy, B. V.; Chassaing, C.; Vvedensky, V. J. Org. Chem. 2000, 65, 8080. (i) Ramadas, K.; Srinivasan, N. Tetrahedron Lett. 1995, 36, 2841. (j) Kent, D. R.; Cody, W. L.; Doherty, A. M. Tetrahedron Lett. 1996, 37, 8711.
37. For recent examples of amine guanylations employing various reagents see: (a) Yu, Y.; Ostresh, J. M.; Houghten, R. A. J. Org. Chem. 2002, 67, 3138. (b) Linton, B. R.; Carr, A. J.; Orner, B. P.; Hamilton, A. D. J. Org. Chem. 2000, 65, 1566. (c) Tamaki, M.; Han, G.; Hruby, V. J. J. Org. Chem. 2001, 66, 1038. (d) Feichtinger, K.; Zapf, C.; Sings, H. L.; Goodman, M. J. Org. Chem. 1998, 63, 3804. (e) Ghosh, A. K.; Hol, W. G. J.; Fan, E. J. Org. Chem. 2001, 66, 2161. (f) Wu, Y.-Q.; Hamilton, S. K.; Wilkinson, D. E.; Hamilton, G. S. J. Org. Chem. 2002, 67, 7553. (g) Musiol, H.-J.; Moroder, L. Org. Lett. 2001, 3, 3859. (h) Katritzky, A. R.; Rogovoy, B. V.; Chassaing, C.; Vvedensky, V. J. Org. Chem. 2000, 65, 8080. (i) Ramadas, K.; Srinivasan, N. Tetrahedron Lett. 1995, 36, 2841. (j) Kent, D. R.; Cody, W. L.; Doherty, A. M. Tetrahedron Lett. 1996, 37, 8711.
38. For recent examples of amine guanylations employing various reagents see: (a) Yu, Y.; Ostresh, J. M.; Houghten, R. A. J. Org. Chem. 2002, 67, 3138. (b) Linton, B. R.; Carr, A. J.; Orner, B. P.; Hamilton, A. D. J. Org. Chem. 2000, 65, 1566. (c) Tamaki, M.; Han, G.; Hruby, V. J. J. Org. Chem. 2001, 66, 1038. (d) Feichtinger, K.; Zapf, C.; Sings, H. L.; Goodman, M. J. Org. Chem. 1998, 63, 3804. (e) Ghosh, A. K.; Hol, W. G. J.; Fan, E. J. Org. Chem. 2001, 66, 2161. (f) Wu, Y.-Q.; Hamilton, S. K.; Wilkinson, D. E.; Hamilton, G. S. J. Org. Chem. 2002, 67, 7553. (g) Musiol, H.-J.; Moroder, L. Org. Lett. 2001, 3, 3859. (h) Katritzky, A. R.; Rogovoy, B. V.; Chassaing, C.; Vvedensky, V. J. Org. Chem. 2000, 65, 8080. (i) Ramadas, K.; Srinivasan, N. Tetrahedron Lett. 1995, 36, 2841. (j) Kent, D. R.; Cody, W. L.; Doherty, A. M. Tetrahedron Lett. 1996, 37, 8711.
39. (a) Tin, M. K. T.; Thirupathi, N.; Yap, G. P. A.; Richeson, D. S. Dalton Trans. 1999, 17, 29471.
40. (b) Tin, M. K. T.; Yap, G. P. A.; Richeson, D. S. Inorg. Chem. 1998, 37, 6728.
41. The crystal structure of 7 is presented in the Supporting Information.
42. Blake, A. J.; Collier, P. E.; Dunn, S. C.; Li, W.-S.; Mountford, P.; Shishkin, O. V. J. Chem. Soc., Dalton Trans. 1997, 1549.
43. Chao, Y.-W.; Wexler, P. A.; Wigley, D. E. Inorg. Chem. 1989, 28, 3860.