The first catalytic carbonylative [4 + 1] cycloaddition using a 1,3- conjugated system. A new transformation of α,β-unsaturated imines to unsaturated γ-lactams catalyzed by Ru3(CO)12 [6]

Journal of the American Chemical Society

Volumn 121, Issue 8, 1999, Pages 1758-1759

  Morimoto, Tsumoru ^a   Chatani, Naoto ^a   Murai, Shinji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKENE; ALLENE DERIVATIVE; BUTYLAMINE; CARBON MONOXIDE; CARBONYL DERIVATIVE; CINNAMALDEHYDE; CYCLOHEXANE; DIOXANE DERIVATIVE; IMINE; TOLUENE;

CATALYSIS; CATALYST; CHEMICAL REACTION; CONJUGATION; LETTER; STOICHIOMETRY;

EID: 0033518865     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983546i     Document Type: Letter

References (60)

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8. For reviews on the Pauson-Khand reaction, see: Schore, N. E. Chem. Rev. 1988, 88, 1081. Schore, N. E. Org. React. 1991, 40, 1. Geis, O.; Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911. Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 1037. Schore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: New York, 1995; Vol. 12, p 703.
9. Recently, the catalytic transformations of enynes were reported using a variety of transition-metal complexes as catalysts. (a) [Co]: Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159. Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793. Lee, N. Y.; Chung, Y. K. Tetrahedron Lett. 1996, 37, 3145. Pagenkopf, B. L.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285. Jeong, N.; Hwang, S. H.; Lee, Y. W.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549. Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. (b) [Ti]: Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 9450. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. (c) [Ru]: Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. (d) [Rh]: Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642.
10. Recently, the catalytic transformations of enynes were reported using a variety of transition-metal complexes as catalysts. (a) [Co]: Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159. Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793. Lee, N. Y.; Chung, Y. K. Tetrahedron Lett. 1996, 37, 3145. Pagenkopf, B. L.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285. Jeong, N.; Hwang, S. H.; Lee, Y. W.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549. Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. (b) [Ti]: Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 9450. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. (c) [Ru]: Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. (d) [Rh]: Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642.
11. Recently, the catalytic transformations of enynes were reported using a variety of transition-metal complexes as catalysts. (a) [Co]: Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159. Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793. Lee, N. Y.; Chung, Y. K. Tetrahedron Lett. 1996, 37, 3145. Pagenkopf, B. L.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285. Jeong, N.; Hwang, S. H.; Lee, Y. W.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549. Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. (b) [Ti]: Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 9450. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. (c) [Ru]: Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. (d) [Rh]: Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642.
12. Recently, the catalytic transformations of enynes were reported using a variety of transition-metal complexes as catalysts. (a) [Co]: Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159. Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793. Lee, N. Y.; Chung, Y. K. Tetrahedron Lett. 1996, 37, 3145. Pagenkopf, B. L.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285. Jeong, N.; Hwang, S. H.; Lee, Y. W.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549. Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. (b) [Ti]: Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 9450. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. (c) [Ru]: Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. (d) [Rh]: Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642.
13. Recently, the catalytic transformations of enynes were reported using a variety of transition-metal complexes as catalysts. (a) [Co]: Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159. Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793. Lee, N. Y.; Chung, Y. K. Tetrahedron Lett. 1996, 37, 3145. Pagenkopf, B. L.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285. Jeong, N.; Hwang, S. H.; Lee, Y. W.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549. Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. (b) [Ti]: Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 9450. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. (c) [Ru]: Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. (d) [Rh]: Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642.
14. Recently, the catalytic transformations of enynes were reported using a variety of transition-metal complexes as catalysts. (a) [Co]: Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159. Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793. Lee, N. Y.; Chung, Y. K. Tetrahedron Lett. 1996, 37, 3145. Pagenkopf, B. L.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285. Jeong, N.; Hwang, S. H.; Lee, Y. W.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549. Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. (b) [Ti]: Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 9450. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. (c) [Ru]: Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. (d) [Rh]: Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642.
15. Recently, the catalytic transformations of enynes were reported using a variety of transition-metal complexes as catalysts. (a) [Co]: Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159. Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793. Lee, N. Y.; Chung, Y. K. Tetrahedron Lett. 1996, 37, 3145. Pagenkopf, B. L.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285. Jeong, N.; Hwang, S. H.; Lee, Y. W.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549. Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. (b) [Ti]: Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 9450. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. (c) [Ru]: Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. (d) [Rh]: Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642.
16. Recently, the catalytic transformations of enynes were reported using a variety of transition-metal complexes as catalysts. (a) [Co]: Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159. Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793. Lee, N. Y.; Chung, Y. K. Tetrahedron Lett. 1996, 37, 3145. Pagenkopf, B. L.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285. Jeong, N.; Hwang, S. H.; Lee, Y. W.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549. Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. (b) [Ti]: Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 9450. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. (c) [Ru]: Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. (d) [Rh]: Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642.
17. Recently, the catalytic transformations of enynes were reported using a variety of transition-metal complexes as catalysts. (a) [Co]: Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159. Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793. Lee, N. Y.; Chung, Y. K. Tetrahedron Lett. 1996, 37, 3145. Pagenkopf, B. L.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285. Jeong, N.; Hwang, S. H.; Lee, Y. W.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549. Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. (b) [Ti]: Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 9450. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. (c) [Ru]: Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. (d) [Rh]: Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642.
18. Recently, the catalytic transformations of enynes were reported using a variety of transition-metal complexes as catalysts. (a) [Co]: Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159. Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793. Lee, N. Y.; Chung, Y. K. Tetrahedron Lett. 1996, 37, 3145. Pagenkopf, B. L.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285. Jeong, N.; Hwang, S. H.; Lee, Y. W.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549. Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. (b) [Ti]: Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 9450. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. (c) [Ru]: Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. (d) [Rh]: Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642.
19. Recently, the catalytic transformations of enynes were reported using a variety of transition-metal complexes as catalysts. (a) [Co]: Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159. Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793. Lee, N. Y.; Chung, Y. K. Tetrahedron Lett. 1996, 37, 3145. Pagenkopf, B. L.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285. Jeong, N.; Hwang, S. H.; Lee, Y. W.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549. Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. (b) [Ti]: Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 9450. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. (c) [Ru]: Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. (d) [Rh]: Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642.
20. Recently, the catalytic transformations of enynes were reported using a variety of transition-metal complexes as catalysts. (a) [Co]: Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159. Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793. Lee, N. Y.; Chung, Y. K. Tetrahedron Lett. 1996, 37, 3145. Pagenkopf, B. L.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285. Jeong, N.; Hwang, S. H.; Lee, Y. W.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549. Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. (b) [Ti]: Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 9450. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. (c) [Ru]: Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. (d) [Rh]: Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642.
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30. Mandai, T.; Tsuji, J.; Tsujiguchi, Y.; Saito, S. J. Am. Chem. Soc. 1993, 115, 5865. Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 2691. Darcel, C.; Bruneau, C.; Dixneuf, P. H. Synlett 1996, 218. Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 11672. Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 2950.
31. Mandai, T.; Tsuji, J.; Tsujiguchi, Y.; Saito, S. J. Am. Chem. Soc. 1993, 115, 5865. Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 2691. Darcel, C.; Bruneau, C.; Dixneuf, P. H. Synlett 1996, 218. Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 11672. Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 2950.
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33. Eaton, B. E.; Rollman, B.; Kaduk, J. A. J. Am. Chem. Soc. 1992, 114, 6245. Sigman, M. S.; Eaton, B. E. J. Am. Chem. Soc. 1996, 118, 11783.
34. Sigman, M. S.; Kerr, C. E.; Eaton, B. E. J. Am. Chem. Soc. 1993, 11, 5, 7545. Sigman, M. S.; Eaton, B. E.; Heise, J. D.; Kubiak, C. P. Organometallics 1996, 15, 2829.
35. Sigman, M. S.; Kerr, C. E.; Eaton, B. E. J. Am. Chem. Soc. 1993, 11, 5, 7545. Sigman, M. S.; Eaton, B. E.; Heise, J. D.; Kubiak, C. P. Organometallics 1996, 15, 2829.
36. Sigman, M. S.; Eaton, B. E. J. Org. Chem. 1994, 59, 7488.
37. All new compounds were characterized by NMR, IR, and mass spectral data and by elemental analyses or high-resolution mass spectra. See Supporting Information.
38. The reaction was run in o-xylene.
39. 8 to yield phthalimidine. Murahashi, S. J. Am. Chem. Soc. 1955, 77, 6403. Horiie, S.; Murahashi, S. Bull. Chem. Soc. Jpn. 1960, 33, 247. (b) We have previously observed formal [4 + 1] cyclocoupling of (β-phenylvinyl)lithium and its nitrogen- containing analogues with carbon monoxide. Ryu, I.; Hayama, Y.; Hirai, A.; Sonoda, N.; Orita, A.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1990, 112, 7061. Orita, A.; Fukudome, M.; Ohe, K.; Murai, S. J. Org. Chem. 1994, 59, 477.
40. 8 to yield phthalimidine. Murahashi, S. J. Am. Chem. Soc. 1955, 77, 6403. Horiie, S.; Murahashi, S. Bull. Chem. Soc. Jpn. 1960, 33, 247. (b) We have previously observed formal [4 + 1] cyclocoupling of (β-phenylvinyl)lithium and its nitrogen- containing analogues with carbon monoxide. Ryu, I.; Hayama, Y.; Hirai, A.; Sonoda, N.; Orita, A.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1990, 112, 7061. Orita, A.; Fukudome, M.; Ohe, K.; Murai, S. J. Org. Chem. 1994, 59, 477.
41. 8 to yield phthalimidine. Murahashi, S. J. Am. Chem. Soc. 1955, 77, 6403. Horiie, S.; Murahashi, S. Bull. Chem. Soc. Jpn. 1960, 33, 247. (b) We have previously observed formal [4 + 1] cyclocoupling of (β-phenylvinyl)lithium and its nitrogen-containing analogues with carbon monoxide. Ryu, I.; Hayama, Y.; Hirai, A.; Sonoda, N.; Orita, A.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1990, 112, 7061. Orita, A.; Fukudome, M.; Ohe, K.; Murai, S. J. Org. Chem. 1994, 59, 477.
42. 8 to yield phthalimidine. Murahashi, S. J. Am. Chem. Soc. 1955, 77, 6403. Horiie, S.; Murahashi, S. Bull. Chem. Soc. Jpn. 1960, 33, 247. (b) We have previously observed formal [4 + 1] cyclocoupling of (β-phenylvinyl)lithium and its nitrogen- containing analogues with carbon monoxide. Ryu, I.; Hayama, Y.; Hirai, A.; Sonoda, N.; Orita, A.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1990, 112, 7061. Orita, A.; Fukudome, M.; Ohe, K.; Murai, S. J. Org. Chem. 1994, 59, 477.
43. Ketimines 9, 13, 19 were used as syn and anti mixture in favor of the anti isomer (60-70%).
44. n (n = 4 or 5) is a key catalytic species. We still need additional experiments.
45. Laine, R. M. J. Mol. Catal. 1982, 14, 137.
46. Hilal, H. S.; Jondi, W.; Khalaf, S.; Abu-Halawa, R. J. Organomet. Chem. 1993, 452, 161. Hilal, H. S.; Khalaf, S.; Jondi, W. J. Organomet. Chem. 1993, 452, 167. Adams, R. D.; Barnard, T. S.; Li, Z.; Wu, W.; Yamamoto, J. H. J. Am. Chem. Soc. 1994, 116, 9103.
47. Hilal, H. S.; Jondi, W.; Khalaf, S.; Abu-Halawa, R. J. Organomet. Chem. 1993, 452, 161. Hilal, H. S.; Khalaf, S.; Jondi, W. J. Organomet. Chem. 1993, 452, 167. Adams, R. D.; Barnard, T. S.; Li, Z.; Wu, W.; Yamamoto, J. H. J. Am. Chem. Soc. 1994, 116, 9103.
48. Hilal, H. S.; Jondi, W.; Khalaf, S.; Abu-Halawa, R. J. Organomet. Chem. 1993, 452, 161. Hilal, H. S.; Khalaf, S.; Jondi, W. J. Organomet. Chem. 1993, 452, 167. Adams, R. D.; Barnard, T. S.; Li, Z.; Wu, W.; Yamamoto, J. H. J. Am. Chem. Soc. 1994, 116, 9103.
49. 1-complexes in which the nitrogen of the imine coordinates to iron. Otsuka, S.; Yoshida, T.; Nakamura, A. Inorg. Chem. 1967, 6, 20. Brodie, A. M.; Johnson, B. F. G.; Josty, P. L.; Lewis, J. J. Chem. Soc. Dalton Trans. 1972, 2031. Cardaci, G.; Bellachioma, G. J. Chem. Soc., Dalton Trans. 1976, 1735. Yin, J.; Chen, J.; Xu, W.; Zheng, Z.; Tang, Y. Organometallics 1988, 7, 21. Danks, T. N.; Thomas, S. E. Tetrahedron Lett. 1988, 29, 1425. Semmelhack, M. F.; Cheng, C. H. J. Organomet. Chem. 1990, 393, 237. Knölker, H.-J.; Baum, G.; Gonser, P. Tetrahedron Lett. 1995, 36, 8191.
50. 1-complexes in which the nitrogen of the imine coordinates to iron. Otsuka, S.; Yoshida, T.; Nakamura, A. Inorg. Chem. 1967, 6, 20. Brodie, A. M.; Johnson, B. F. G.; Josty, P. L.; Lewis, J. J. Chem. Soc. Dalton Trans. 1972, 2031. Cardaci, G.; Bellachioma, G. J. Chem. Soc., Dalton Trans. 1976, 1735. Yin, J.; Chen, J.; Xu, W.; Zheng, Z.; Tang, Y. Organometallics 1988, 7, 21. Danks, T. N.; Thomas, S. E. Tetrahedron Lett. 1988, 29, 1425. Semmelhack, M. F.; Cheng, C. H. J. Organomet. Chem. 1990, 393, 237. Knölker, H.-J.; Baum, G.; Gonser, P. Tetrahedron Lett. 1995, 36, 8191.
51. 1-complexes in which the nitrogen of the imine coordinates to iron. Otsuka, S.; Yoshida, T.; Nakamura, A. Inorg. Chem. 1967, 6, 20. Brodie, A. M.; Johnson, B. F. G.; Josty, P. L.; Lewis, J. J. Chem. Soc. Dalton Trans. 1972, 2031. Cardaci, G.; Bellachioma, G. J. Chem. Soc., Dalton Trans. 1976, 1735. Yin, J.; Chen, J.; Xu, W.; Zheng, Z.; Tang, Y. Organometallics 1988, 7, 21. Danks, T. N.; Thomas, S. E. Tetrahedron Lett. 1988, 29, 1425. Semmelhack, M. F.; Cheng, C. H. J. Organomet. Chem. 1990, 393, 237. Knölker, H.-J.; Baum, G.; Gonser, P. Tetrahedron Lett. 1995, 36, 8191.
52. 1-complexes in which the nitrogen of the imine coordinates to iron. Otsuka, S.; Yoshida, T.; Nakamura, A. Inorg. Chem. 1967, 6, 20. Brodie, A. M.; Johnson, B. F. G.; Josty, P. L.; Lewis, J. J. Chem. Soc. Dalton Trans. 1972, 2031. Cardaci, G.; Bellachioma, G. J. Chem. Soc., Dalton Trans. 1976, 1735. Yin, J.; Chen, J.; Xu, W.; Zheng, Z.; Tang, Y. Organometallics 1988, 7, 21. Danks, T. N.; Thomas, S. E. Tetrahedron Lett. 1988, 29, 1425. Semmelhack, M. F.; Cheng, C. H. J. Organomet. Chem. 1990, 393, 237. Knölker, H.-J.; Baum, G.; Gonser, P. Tetrahedron Lett. 1995, 36, 8191.
53. 1-complexes in which the nitrogen of the imine coordinates to iron. Otsuka, S.; Yoshida, T.; Nakamura, A. Inorg. Chem. 1967, 6, 20. Brodie, A. M.; Johnson, B. F. G.; Josty, P. L.; Lewis, J. J. Chem. Soc. Dalton Trans. 1972, 2031. Cardaci, G.; Bellachioma, G. J. Chem. Soc., Dalton Trans. 1976, 1735. Yin, J.; Chen, J.; Xu, W.; Zheng, Z.; Tang, Y. Organometallics 1988, 7, 21. Danks, T. N.; Thomas, S. E. Tetrahedron Lett. 1988, 29, 1425. Semmelhack, M. F.; Cheng, C. H. J. Organomet. Chem. 1990, 393, 237. Knölker, H.-J.; Baum, G.; Gonser, P. Tetrahedron Lett. 1995, 36, 8191.
54. 1-complexes in which the nitrogen of the imine coordinates to iron. Otsuka, S.; Yoshida, T.; Nakamura, A. Inorg. Chem. 1967, 6, 20. Brodie, A. M.; Johnson, B. F. G.; Josty, P. L.; Lewis, J. J. Chem. Soc. Dalton Trans. 1972, 2031. Cardaci, G.; Bellachioma, G. J. Chem. Soc., Dalton Trans. 1976, 1735. Yin, J.; Chen, J.; Xu, W.; Zheng, Z.; Tang, Y. Organometallics 1988, 7, 21. Danks, T. N.; Thomas, S. E. Tetrahedron Lett. 1988, 29, 1425. Semmelhack, M. F.; Cheng, C. H. J. Organomet. Chem. 1990, 393, 237. Knölker, H.-J.; Baum, G.; Gonser, P. Tetrahedron Lett. 1995, 36, 8191.
55. 1-complexes in which the nitrogen of the imine coordinates to iron. Otsuka, S.; Yoshida, T.; Nakamura, A. Inorg. Chem. 1967, 6, 20. Brodie, A. M.; Johnson, B. F. G.; Josty, P. L.; Lewis, J. J. Chem. Soc. Dalton Trans. 1972, 2031. Cardaci, G.; Bellachioma, G. J. Chem. Soc., Dalton Trans. 1976, 1735. Yin, J.; Chen, J.; Xu, W.; Zheng, Z.; Tang, Y. Organometallics 1988, 7, 21. Danks, T. N.; Thomas, S. E. Tetrahedron Lett. 1988, 29, 1425. Semmelhack, M. F.; Cheng, C. H. J. Organomet. Chem. 1990, 393, 237. Knölker, H.-J.; Baum, G.; Gonser, P. Tetrahedron Lett. 1995, 36, 8191.
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60. 2-nitrogen to the ruthenium carbonyl plays a key role. Fukuyama, T.; Chatani, N.; Tatsumi, J.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1998, 120, 11522 and references therein.