Ru3(CO)12-catalyzed reaction of yne-imines with carbon monoxide leading to bicyclic α,β-unsaturated lactams

Journal of Organometallic Chemistry

Volumn 579, Issue 1-2, 1999, Pages 177-181

  Chatani, Naoto ^a   Morimoto, Tsumoru ^a   Kamitani, Akihito ^a   Fukumoto, Yoshiya ^a   Murai, Shinji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Carbon monoxide; Cyclocarbonylation; Lactam; Ruthenium carbonyl; Yne imine

Indexed keywords

EID: 0001091111     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(98)01220-0     Document Type: Article

References (23)

1. T. Morimoto, N. Chatani, Y. Fukumoto, S. Murai, J. Org. Chem. 62 (1997) 3762.
2. For Co-catalyzed reactions, see: (a) N. Jeong, S.H. Hwang, Y. Lee, Y.K. Chung, J. Am. Chem. Soc. 116 (1994) 3159. (b) B.Y. Lee, Y.K. Chung, N. Jeong, Y. Lee, S.H. Hwang, J. Am. Chem. Soc. 116 (1994) 8793. (c) N.Y. Lee, Y.K. Chung, Tetrahedron Lett. 37 (1996) 3145. (d) B.L. Pagenkopf, T. Livinghouse, J. Am. Chem. Soc. 118 (1996) 2285. (e) N. Jeong, S.H. Hwang, Y.W. Lee, J.S. Lim, J. Am. Chem. Soc. 119 (1997) 10549. (f) J.W. Kim, Y.K. Chung, Synthesis (1998) 142. (g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 120 (1998) 10782. For Ti-catalyzed reactions, see: (h) F.A. Hicks, N.M. Kablaoui, S.L. Buchwald, J. Am. Chem. Soc. 118 (1996) 9450. (i) F.A. Hicks, S.L. Buchwald, J. Am. Chem. Soc. 118 (1996) 11688. For Rh-catalyzed reactions, see: (j) Y. Koga, T. Kobayashi, K. Narasaka, Chem. Lett. (1998) 249. (k) N. Jeong, S. Lee, B.K. Sung, Organometallics 17 (1998) 3642.
3. For Co-catalyzed reactions, see: (a) N. Jeong, S.H. Hwang, Y. Lee, Y.K. Chung, J. Am. Chem. Soc. 116 (1994) 3159. (b) B.Y. Lee, Y.K. Chung, N. Jeong, Y. Lee, S.H. Hwang, J. Am. Chem. Soc. 116 (1994) 8793. (c) N.Y. Lee, Y.K. Chung, Tetrahedron Lett. 37 (1996) 3145. (d) B.L. Pagenkopf, T. Livinghouse, J. Am. Chem. Soc. 118 (1996) 2285. (e) N. Jeong, S.H. Hwang, Y.W. Lee, J.S. Lim, J. Am. Chem. Soc. 119 (1997) 10549. (f) J.W. Kim, Y.K. Chung, Synthesis (1998) 142. (g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 120 (1998) 10782. For Ti-catalyzed reactions, see: (h) F.A. Hicks, N.M. Kablaoui, S.L. Buchwald, J. Am. Chem. Soc. 118 (1996) 9450. (i) F.A. Hicks, S.L. Buchwald, J. Am. Chem. Soc. 118 (1996) 11688. For Rh-catalyzed reactions, see: (j) Y. Koga, T. Kobayashi, K. Narasaka, Chem. Lett. (1998) 249. (k) N. Jeong, S. Lee, B.K. Sung, Organometallics 17 (1998) 3642.
4. For Co-catalyzed reactions, see: (a) N. Jeong, S.H. Hwang, Y. Lee, Y.K. Chung, J. Am. Chem. Soc. 116 (1994) 3159. (b) B.Y. Lee, Y.K. Chung, N. Jeong, Y. Lee, S.H. Hwang, J. Am. Chem. Soc. 116 (1994) 8793. (c) N.Y. Lee, Y.K. Chung, Tetrahedron Lett. 37 (1996) 3145. (d) B.L. Pagenkopf, T. Livinghouse, J. Am. Chem. Soc. 118 (1996) 2285. (e) N. Jeong, S.H. Hwang, Y.W. Lee, J.S. Lim, J. Am. Chem. Soc. 119 (1997) 10549. (f) J.W. Kim, Y.K. Chung, Synthesis (1998) 142. (g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 120 (1998) 10782. For Ti-catalyzed reactions, see: (h) F.A. Hicks, N.M. Kablaoui, S.L. Buchwald, J. Am. Chem. Soc. 118 (1996) 9450. (i) F.A. Hicks, S.L. Buchwald, J. Am. Chem. Soc. 118 (1996) 11688. For Rh-catalyzed reactions, see: (j) Y. Koga, T. Kobayashi, K. Narasaka, Chem. Lett. (1998) 249. (k) N. Jeong, S. Lee, B.K. Sung, Organometallics 17 (1998) 3642.
5. For Co-catalyzed reactions, see: (a) N. Jeong, S.H. Hwang, Y. Lee, Y.K. Chung, J. Am. Chem. Soc. 116 (1994) 3159. (b) B.Y. Lee, Y.K. Chung, N. Jeong, Y. Lee, S.H. Hwang, J. Am. Chem. Soc. 116 (1994) 8793. (c) N.Y. Lee, Y.K. Chung, Tetrahedron Lett. 37 (1996) 3145. (d) B.L. Pagenkopf, T. Livinghouse, J. Am. Chem. Soc. 118 (1996) 2285. (e) N. Jeong, S.H. Hwang, Y.W. Lee, J.S. Lim, J. Am. Chem. Soc. 119 (1997) 10549. (f) J.W. Kim, Y.K. Chung, Synthesis (1998) 142. (g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 120 (1998) 10782. For Ti-catalyzed reactions, see: (h) F.A. Hicks, N.M. Kablaoui, S.L. Buchwald, J. Am. Chem. Soc. 118 (1996) 9450. (i) F.A. Hicks, S.L. Buchwald, J. Am. Chem. Soc. 118 (1996) 11688. For Rh-catalyzed reactions, see: (j) Y. Koga, T. Kobayashi, K. Narasaka, Chem. Lett. (1998) 249. (k) N. Jeong, S. Lee, B.K. Sung, Organometallics 17 (1998) 3642.
6. For Co-catalyzed reactions, see: (a) N. Jeong, S.H. Hwang, Y. Lee, Y.K. Chung, J. Am. Chem. Soc. 116 (1994) 3159. (b) B.Y. Lee, Y.K. Chung, N. Jeong, Y. Lee, S.H. Hwang, J. Am. Chem. Soc. 116 (1994) 8793. (c) N.Y. Lee, Y.K. Chung, Tetrahedron Lett. 37 (1996) 3145. (d) B.L. Pagenkopf, T. Livinghouse, J. Am. Chem. Soc. 118 (1996) 2285. (e) N. Jeong, S.H. Hwang, Y.W. Lee, J.S. Lim, J. Am. Chem. Soc. 119 (1997) 10549. (f) J.W. Kim, Y.K. Chung, Synthesis (1998) 142. (g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 120 (1998) 10782. For Ti-catalyzed reactions, see: (h) F.A. Hicks, N.M. Kablaoui, S.L. Buchwald, J. Am. Chem. Soc. 118 (1996) 9450. (i) F.A. Hicks, S.L. Buchwald, J. Am. Chem. Soc. 118 (1996) 11688. For Rh-catalyzed reactions, see: (j) Y. Koga, T. Kobayashi, K. Narasaka, Chem. Lett. (1998) 249. (k) N. Jeong, S. Lee, B.K. Sung, Organometallics 17 (1998) 3642.
7. For Co-catalyzed reactions, see: (a) N. Jeong, S.H. Hwang, Y. Lee, Y.K. Chung, J. Am. Chem. Soc. 116 (1994) 3159. (b) B.Y. Lee, Y.K. Chung, N. Jeong, Y. Lee, S.H. Hwang, J. Am. Chem. Soc. 116 (1994) 8793. (c) N.Y. Lee, Y.K. Chung, Tetrahedron Lett. 37 (1996) 3145. (d) B.L. Pagenkopf, T. Livinghouse, J. Am. Chem. Soc. 118 (1996) 2285. (e) N. Jeong, S.H. Hwang, Y.W. Lee, J.S. Lim, J. Am. Chem. Soc. 119 (1997) 10549. (f) J.W. Kim, Y.K. Chung, Synthesis (1998) 142. (g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 120 (1998) 10782. For Ti-catalyzed reactions, see: (h) F.A. Hicks, N.M. Kablaoui, S.L. Buchwald, J. Am. Chem. Soc. 118 (1996) 9450. (i) F.A. Hicks, S.L. Buchwald, J. Am. Chem. Soc. 118 (1996) 11688. For Rh-catalyzed reactions, see: (j) Y. Koga, T. Kobayashi, K. Narasaka, Chem. Lett. (1998) 249. (k) N. Jeong, S. Lee, B.K. Sung, Organometallics 17 (1998) 3642.
8. For Co-catalyzed reactions, see: (a) N. Jeong, S.H. Hwang, Y. Lee, Y.K. Chung, J. Am. Chem. Soc. 116 (1994) 3159. (b) B.Y. Lee, Y.K. Chung, N. Jeong, Y. Lee, S.H. Hwang, J. Am. Chem. Soc. 116 (1994) 8793. (c) N.Y. Lee, Y.K. Chung, Tetrahedron Lett. 37 (1996) 3145. (d) B.L. Pagenkopf, T. Livinghouse, J. Am. Chem. Soc. 118 (1996) 2285. (e) N. Jeong, S.H. Hwang, Y.W. Lee, J.S. Lim, J. Am. Chem. Soc. 119 (1997) 10549. (f) J.W. Kim, Y.K. Chung, Synthesis (1998) 142. (g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 120 (1998) 10782. For Ti-catalyzed reactions, see: (h) F.A. Hicks, N.M. Kablaoui, S.L. Buchwald, J. Am. Chem. Soc. 118 (1996) 9450. (i) F.A. Hicks, S.L. Buchwald, J. Am. Chem. Soc. 118 (1996) 11688. For Rh-catalyzed reactions, see: (j) Y. Koga, T. Kobayashi, K. Narasaka, Chem. Lett. (1998) 249. (k) N. Jeong, S. Lee, B.K. Sung, Organometallics 17 (1998) 3642.
9. For Co-catalyzed reactions, see: (a) N. Jeong, S.H. Hwang, Y. Lee, Y.K. Chung, J. Am. Chem. Soc. 116 (1994) 3159. (b) B.Y. Lee, Y.K. Chung, N. Jeong, Y. Lee, S.H. Hwang, J. Am. Chem. Soc. 116 (1994) 8793. (c) N.Y. Lee, Y.K. Chung, Tetrahedron Lett. 37 (1996) 3145. (d) B.L. Pagenkopf, T. Livinghouse, J. Am. Chem. Soc. 118 (1996) 2285. (e) N. Jeong, S.H. Hwang, Y.W. Lee, J.S. Lim, J. Am. Chem. Soc. 119 (1997) 10549. (f) J.W. Kim, Y.K. Chung, Synthesis (1998) 142. (g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 120 (1998) 10782. For Ti-catalyzed reactions, see: (h) F.A. Hicks, N.M. Kablaoui, S.L. Buchwald, J. Am. Chem. Soc. 118 (1996) 9450. (i) F.A. Hicks, S.L. Buchwald, J. Am. Chem. Soc. 118 (1996) 11688. For Rh-catalyzed reactions, see: (j) Y. Koga, T. Kobayashi, K. Narasaka, Chem. Lett. (1998) 249. (k) N. Jeong, S. Lee, B.K. Sung, Organometallics 17 (1998) 3642.
10. For Co-catalyzed reactions, see: (a) N. Jeong, S.H. Hwang, Y. Lee, Y.K. Chung, J. Am. Chem. Soc. 116 (1994) 3159. (b) B.Y. Lee, Y.K. Chung, N. Jeong, Y. Lee, S.H. Hwang, J. Am. Chem. Soc. 116 (1994) 8793. (c) N.Y. Lee, Y.K. Chung, Tetrahedron Lett. 37 (1996) 3145. (d) B.L. Pagenkopf, T. Livinghouse, J. Am. Chem. Soc. 118 (1996) 2285. (e) N. Jeong, S.H. Hwang, Y.W. Lee, J.S. Lim, J. Am. Chem. Soc. 119 (1997) 10549. (f) J.W. Kim, Y.K. Chung, Synthesis (1998) 142. (g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 120 (1998) 10782. For Ti-catalyzed reactions, see: (h) F.A. Hicks, N.M. Kablaoui, S.L. Buchwald, J. Am. Chem. Soc. 118 (1996) 9450. (i) F.A. Hicks, S.L. Buchwald, J. Am. Chem. Soc. 118 (1996) 11688. For Rh-catalyzed reactions, see: (j) Y. Koga, T. Kobayashi, K. Narasaka, Chem. Lett. (1998) 249. (k) N. Jeong, S. Lee, B.K. Sung, Organometallics 17 (1998) 3642.
11. For Co-catalyzed reactions, see: (a) N. Jeong, S.H. Hwang, Y. Lee, Y.K. Chung, J. Am. Chem. Soc. 116 (1994) 3159. (b) B.Y. Lee, Y.K. Chung, N. Jeong, Y. Lee, S.H. Hwang, J. Am. Chem. Soc. 116 (1994) 8793. (c) N.Y. Lee, Y.K. Chung, Tetrahedron Lett. 37 (1996) 3145. (d) B.L. Pagenkopf, T. Livinghouse, J. Am. Chem. Soc. 118 (1996) 2285. (e) N. Jeong, S.H. Hwang, Y.W. Lee, J.S. Lim, J. Am. Chem. Soc. 119 (1997) 10549. (f) J.W. Kim, Y.K. Chung, Synthesis (1998) 142. (g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 120 (1998) 10782. For Ti-catalyzed reactions, see: (h) F.A. Hicks, N.M. Kablaoui, S.L. Buchwald, J. Am. Chem. Soc. 118 (1996) 9450. (i) F.A. Hicks, S.L. Buchwald, J. Am. Chem. Soc. 118 (1996) 11688. For Rh-catalyzed reactions, see: (j) Y. Koga, T. Kobayashi, K. Narasaka, Chem. Lett. (1998) 249. (k) N. Jeong, S. Lee, B.K. Sung, Organometallics 17 (1998) 3642.
12. For Co-catalyzed reactions, see: (a) N. Jeong, S.H. Hwang, Y. Lee, Y.K. Chung, J. Am. Chem. Soc. 116 (1994) 3159. (b) B.Y. Lee, Y.K. Chung, N. Jeong, Y. Lee, S.H. Hwang, J. Am. Chem. Soc. 116 (1994) 8793. (c) N.Y. Lee, Y.K. Chung, Tetrahedron Lett. 37 (1996) 3145. (d) B.L. Pagenkopf, T. Livinghouse, J. Am. Chem. Soc. 118 (1996) 2285. (e) N. Jeong, S.H. Hwang, Y.W. Lee, J.S. Lim, J. Am. Chem. Soc. 119 (1997) 10549. (f) J.W. Kim, Y.K. Chung, Synthesis (1998) 142. (g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 120 (1998) 10782. For Ti-catalyzed reactions, see: (h) F.A. Hicks, N.M. Kablaoui, S.L. Buchwald, J. Am. Chem. Soc. 118 (1996) 9450. (i) F.A. Hicks, S.L. Buchwald, J. Am. Chem. Soc. 118 (1996) 11688. For Rh-catalyzed reactions, see: (j) Y. Koga, T. Kobayashi, K. Narasaka, Chem. Lett. (1998) 249. (k) N. Jeong, S. Lee, B.K. Sung, Organometallics 17 (1998) 3642.
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