Rhodium-catalyzed reaction of N-acylpiperazines with CO and ethylene. Carbonylation at a C-H bond directed by an amido group

Tetrahedron Letters

Volumn 38, Issue 43, 1997, Pages 7565-7568

  Ishii, Yutaka ^a   Chatani, Naoto ^a   Kakiuchi, Fumitoshi ^a   Murai, Shinji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERAZINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030860516     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01738-3     Document Type: Article

References (33)

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6. For catalytic reaction involving cleavage of a C-H bond promoted by ketone as a directing group, see: Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529. Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Pure & Appl. Chem. 1994, 66, 1527. Tapsak, M.A.; Weber, W.P. Polymer Bull. 1994, 33, 417. Guo, H.; Weber, W.P. Polymer Bull. 1994, 32, 525. Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. Guo, H.; Tapsak, M.A.; Weber, W.P. Polymer Bull. 1995, 34, 49. Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, 679. Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. Sonoda, M.; Kakiuchi, F.; Chatani, N.; Murai, S. J. Organomet. Chem. 1995, 504, 151. Guo, H.; Weber, W.P. Polymer Bull. 1995, 35, 259. Guo, H.; Tapsak, M.A.; Weber, W.P. Macromolecules 1995, 28, 4714. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1996, 506, 339. Wang, G.; Guo, H.; Weber, W.P. J. Organomet. Chem. 1996, 521, 351. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1997, 530, 211.
7. For catalytic reaction involving cleavage of a C-H bond promoted by ketone as a directing group, see: Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529. Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Pure & Appl. Chem. 1994, 66, 1527. Tapsak, M.A.; Weber, W.P. Polymer Bull. 1994, 33, 417. Guo, H.; Weber, W.P. Polymer Bull. 1994, 32, 525. Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. Guo, H.; Tapsak, M.A.; Weber, W.P. Polymer Bull. 1995, 34, 49. Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, 679. Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. Sonoda, M.; Kakiuchi, F.; Chatani, N.; Murai, S. J. Organomet. Chem. 1995, 504, 151. Guo, H.; Weber, W.P. Polymer Bull. 1995, 35, 259. Guo, H.; Tapsak, M.A.; Weber, W.P. Macromolecules 1995, 28, 4714. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1996, 506, 339. Wang, G.; Guo, H.; Weber, W.P. J. Organomet. Chem. 1996, 521, 351. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1997, 530, 211.
8. For catalytic reaction involving cleavage of a C-H bond promoted by ketone as a directing group, see: Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529. Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Pure & Appl. Chem. 1994, 66, 1527. Tapsak, M.A.; Weber, W.P. Polymer Bull. 1994, 33, 417. Guo, H.; Weber, W.P. Polymer Bull. 1994, 32, 525. Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. Guo, H.; Tapsak, M.A.; Weber, W.P. Polymer Bull. 1995, 34, 49. Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, 679. Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. Sonoda, M.; Kakiuchi, F.; Chatani, N.; Murai, S. J. Organomet. Chem. 1995, 504, 151. Guo, H.; Weber, W.P. Polymer Bull. 1995, 35, 259. Guo, H.; Tapsak, M.A.; Weber, W.P. Macromolecules 1995, 28, 4714. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1996, 506, 339. Wang, G.; Guo, H.; Weber, W.P. J. Organomet. Chem. 1996, 521, 351. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1997, 530, 211.
9. For catalytic reaction involving cleavage of a C-H bond promoted by ketone as a directing group, see: Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529. Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Pure & Appl. Chem. 1994, 66, 1527. Tapsak, M.A.; Weber, W.P. Polymer Bull. 1994, 33, 417. Guo, H.; Weber, W.P. Polymer Bull. 1994, 32, 525. Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. Guo, H.; Tapsak, M.A.; Weber, W.P. Polymer Bull. 1995, 34, 49. Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, 679. Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. Sonoda, M.; Kakiuchi, F.; Chatani, N.; Murai, S. J. Organomet. Chem. 1995, 504, 151. Guo, H.; Weber, W.P. Polymer Bull. 1995, 35, 259. Guo, H.; Tapsak, M.A.; Weber, W.P. Macromolecules 1995, 28, 4714. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1996, 506, 339. Wang, G.; Guo, H.; Weber, W.P. J. Organomet. Chem. 1996, 521, 351. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1997, 530, 211.
10. For catalytic reaction involving cleavage of a C-H bond promoted by ketone as a directing group, see: Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529. Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Pure & Appl. Chem. 1994, 66, 1527. Tapsak, M.A.; Weber, W.P. Polymer Bull. 1994, 33, 417. Guo, H.; Weber, W.P. Polymer Bull. 1994, 32, 525. Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. Guo, H.; Tapsak, M.A.; Weber, W.P. Polymer Bull. 1995, 34, 49. Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, 679. Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. Sonoda, M.; Kakiuchi, F.; Chatani, N.; Murai, S. J. Organomet. Chem. 1995, 504, 151. Guo, H.; Weber, W.P. Polymer Bull. 1995, 35, 259. Guo, H.; Tapsak, M.A.; Weber, W.P. Macromolecules 1995, 28, 4714. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1996, 506, 339. Wang, G.; Guo, H.; Weber, W.P. J. Organomet. Chem. 1996, 521, 351. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1997, 530, 211.
11. For catalytic reaction involving cleavage of a C-H bond promoted by ketone as a directing group, see: Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529. Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Pure & Appl. Chem. 1994, 66, 1527. Tapsak, M.A.; Weber, W.P. Polymer Bull. 1994, 33, 417. Guo, H.; Weber, W.P. Polymer Bull. 1994, 32, 525. Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. Guo, H.; Tapsak, M.A.; Weber, W.P. Polymer Bull. 1995, 34, 49. Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, 679. Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. Sonoda, M.; Kakiuchi, F.; Chatani, N.; Murai, S. J. Organomet. Chem. 1995, 504, 151. Guo, H.; Weber, W.P. Polymer Bull. 1995, 35, 259. Guo, H.; Tapsak, M.A.; Weber, W.P. Macromolecules 1995, 28, 4714. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1996, 506, 339. Wang, G.; Guo, H.; Weber, W.P. J. Organomet. Chem. 1996, 521, 351. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1997, 530, 211.
12. For catalytic reaction involving cleavage of a C-H bond promoted by ketone as a directing group, see: Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529. Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Pure & Appl. Chem. 1994, 66, 1527. Tapsak, M.A.; Weber, W.P. Polymer Bull. 1994, 33, 417. Guo, H.; Weber, W.P. Polymer Bull. 1994, 32, 525. Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. Guo, H.; Tapsak, M.A.; Weber, W.P. Polymer Bull. 1995, 34, 49. Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, 679. Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. Sonoda, M.; Kakiuchi, F.; Chatani, N.; Murai, S. J. Organomet. Chem. 1995, 504, 151. Guo, H.; Weber, W.P. Polymer Bull. 1995, 35, 259. Guo, H.; Tapsak, M.A.; Weber, W.P. Macromolecules 1995, 28, 4714. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1996, 506, 339. Wang, G.; Guo, H.; Weber, W.P. J. Organomet. Chem. 1996, 521, 351. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1997, 530, 211.
13. For catalytic reaction involving cleavage of a C-H bond promoted by ketone as a directing group, see: Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529. Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Pure & Appl. Chem. 1994, 66, 1527. Tapsak, M.A.; Weber, W.P. Polymer Bull. 1994, 33, 417. Guo, H.; Weber, W.P. Polymer Bull. 1994, 32, 525. Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. Guo, H.; Tapsak, M.A.; Weber, W.P. Polymer Bull. 1995, 34, 49. Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, 679. Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. Sonoda, M.; Kakiuchi, F.; Chatani, N.; Murai, S. J. Organomet. Chem. 1995, 504, 151. Guo, H.; Weber, W.P. Polymer Bull. 1995, 35, 259. Guo, H.; Tapsak, M.A.; Weber, W.P. Macromolecules 1995, 28, 4714. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1996, 506, 339. Wang, G.; Guo, H.; Weber, W.P. J. Organomet. Chem. 1996, 521, 351. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1997, 530, 211.
14. For catalytic reaction involving cleavage of a C-H bond promoted by ketone as a directing group, see: Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529. Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Pure & Appl. Chem. 1994, 66, 1527. Tapsak, M.A.; Weber, W.P. Polymer Bull. 1994, 33, 417. Guo, H.; Weber, W.P. Polymer Bull. 1994, 32, 525. Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. Guo, H.; Tapsak, M.A.; Weber, W.P. Polymer Bull. 1995, 34, 49. Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, 679. Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. Sonoda, M.; Kakiuchi, F.; Chatani, N.; Murai, S. J. Organomet. Chem. 1995, 504, 151. Guo, H.; Weber, W.P. Polymer Bull. 1995, 35, 259. Guo, H.; Tapsak, M.A.; Weber, W.P. Macromolecules 1995, 28, 4714. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1996, 506, 339. Wang, G.; Guo, H.; Weber, W.P. J. Organomet. Chem. 1996, 521, 351. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1997, 530, 211.
15. For catalytic reaction involving cleavage of a C-H bond promoted by ketone as a directing group, see: Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529. Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Pure & Appl. Chem. 1994, 66, 1527. Tapsak, M.A.; Weber, W.P. Polymer Bull. 1994, 33, 417. Guo, H.; Weber, W.P. Polymer Bull. 1994, 32, 525. Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. Guo, H.; Tapsak, M.A.; Weber, W.P. Polymer Bull. 1995, 34, 49. Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, 679. Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. Sonoda, M.; Kakiuchi, F.; Chatani, N.; Murai, S. J. Organomet. Chem. 1995, 504, 151. Guo, H.; Weber, W.P. Polymer Bull. 1995, 35, 259. Guo, H.; Tapsak, M.A.; Weber, W.P. Macromolecules 1995, 28, 4714. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1996, 506, 339. Wang, G.; Guo, H.; Weber, W.P. J. Organomet. Chem. 1996, 521, 351. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1997, 530, 211.
16. For catalytic reaction involving cleavage of a C-H bond promoted by ketone as a directing group, see: Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529. Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Pure & Appl. Chem. 1994, 66, 1527. Tapsak, M.A.; Weber, W.P. Polymer Bull. 1994, 33, 417. Guo, H.; Weber, W.P. Polymer Bull. 1994, 32, 525. Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. Guo, H.; Tapsak, M.A.; Weber, W.P. Polymer Bull. 1995, 34, 49. Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, 679. Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. Sonoda, M.; Kakiuchi, F.; Chatani, N.; Murai, S. J. Organomet. Chem. 1995, 504, 151. Guo, H.; Weber, W.P. Polymer Bull. 1995, 35, 259. Guo, H.; Tapsak, M.A.; Weber, W.P. Macromolecules 1995, 28, 4714. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1996, 506, 339. Wang, G.; Guo, H.; Weber, W.P. J. Organomet. Chem. 1996, 521, 351. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1997, 530, 211.
17. For catalytic reaction involving cleavage of a C-H bond promoted by ketone as a directing group, see: Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529. Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Pure & Appl. Chem. 1994, 66, 1527. Tapsak, M.A.; Weber, W.P. Polymer Bull. 1994, 33, 417. Guo, H.; Weber, W.P. Polymer Bull. 1994, 32, 525. Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. Guo, H.; Tapsak, M.A.; Weber, W.P. Polymer Bull. 1995, 34, 49. Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, 679. Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. Sonoda, M.; Kakiuchi, F.; Chatani, N.; Murai, S. J. Organomet. Chem. 1995, 504, 151. Guo, H.; Weber, W.P. Polymer Bull. 1995, 35, 259. Guo, H.; Tapsak, M.A.; Weber, W.P. Macromolecules 1995, 28, 4714. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1996, 506, 339. Wang, G.; Guo, H.; Weber, W.P. J. Organomet. Chem. 1996, 521, 351. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1997, 530, 211.
18. For catalytic reaction involving cleavage of a C-H bond promoted by ketone as a directing group, see: Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529. Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Pure & Appl. Chem. 1994, 66, 1527. Tapsak, M.A.; Weber, W.P. Polymer Bull. 1994, 33, 417. Guo, H.; Weber, W.P. Polymer Bull. 1994, 32, 525. Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. Guo, H.; Tapsak, M.A.; Weber, W.P. Polymer Bull. 1995, 34, 49. Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, 679. Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. Sonoda, M.; Kakiuchi, F.; Chatani, N.; Murai, S. J. Organomet. Chem. 1995, 504, 151. Guo, H.; Weber, W.P. Polymer Bull. 1995, 35, 259. Guo, H.; Tapsak, M.A.; Weber, W.P. Macromolecules 1995, 28, 4714. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1996, 506, 339. Wang, G.; Guo, H.; Weber, W.P. J. Organomet. Chem. 1996, 521, 351. Harris, P.W.R.; Woodgate, P.D. J. Organomet. Chem. 1997, 530, 211.
19. For catalytic reaction involving cleavage of a C-H bond promoted by ester as a directing group, see: Trost, B.M.; Imi, K.; Davies, I.W. J. Am. Chem. Soc. 1995, 117, 5371. Sonoda, M.; Kakiuchi, F.; Chatani, N.; Murai, S. Chem. Lett. 1996, 109.
20. For catalytic reaction involving cleavage of a C-H bond promoted by ester as a directing group, see: Trost, B.M.; Imi, K.; Davies, I.W. J. Am. Chem. Soc. 1995, 117, 5371. Sonoda, M.; Kakiuchi, F.; Chatani, N.; Murai, S. Chem. Lett. 1996, 109.
21. For catalytic reaction involving cleavage of a C-H bond promoted by pyridine as a directing group, see: Lim, Y.-G.; Kim, Y.H.; Kang, J.-B. J. Chem. Soc., Chem. Commun. 1994, 2267. Lim, Y.-G.; Kim, Y.H.; Kang, J.-B. J. Chem. Soc., Perkin Trans. 1 1996, 2201. Lim, Y.-G.; Kang, J.-B.; Kim, Y.H. J. Chem. Soc., Chem. Commun. 1996, 585. Fujii, N.; Kakiuchi, F.; Chatani, N.; Murai, S. Chem. Lett. 1996, 939. Fujii, N.; Kakiuchi, F.; Yamada, A.; Chatani, N.; Murai, S. Chem. Lett. 1997, 425. See also refs .
22. For catalytic reaction involving cleavage of a C-H bond promoted by pyridine as a directing group, see: Lim, Y.-G.; Kim, Y.H.; Kang, J.-B. J. Chem. Soc., Chem. Commun. 1994, 2267. Lim, Y.-G.; Kim, Y.H.; Kang, J.-B. J. Chem. Soc., Perkin Trans. 1 1996, 2201. Lim, Y.-G.; Kang, J.-B.; Kim, Y.H. J. Chem. Soc., Chem. Commun. 1996, 585. Fujii, N.; Kakiuchi, F.; Chatani, N.; Murai, S. Chem. Lett. 1996, 939. Fujii, N.; Kakiuchi, F.; Yamada, A.; Chatani, N.; Murai, S. Chem. Lett. 1997, 425. See also refs .
23. For catalytic reaction involving cleavage of a C-H bond promoted by pyridine as a directing group, see: Lim, Y.-G.; Kim, Y.H.; Kang, J.-B. J. Chem. Soc., Chem. Commun. 1994, 2267. Lim, Y.-G.; Kim, Y.H.; Kang, J.-B. J. Chem. Soc., Perkin Trans. 1 1996, 2201. Lim, Y.-G.; Kang, J.-B.; Kim, Y.H. J. Chem. Soc., Chem. Commun. 1996, 585. Fujii, N.; Kakiuchi, F.; Chatani, N.; Murai, S. Chem. Lett. 1996, 939. Fujii, N.; Kakiuchi, F.; Yamada, A.; Chatani, N.; Murai, S. Chem. Lett. 1997, 425. See also refs .
24. For catalytic reaction involving cleavage of a C-H bond promoted by pyridine as a directing group, see: Lim, Y.-G.; Kim, Y.H.; Kang, J.-B. J. Chem. Soc., Chem. Commun. 1994, 2267. Lim, Y.-G.; Kim, Y.H.; Kang, J.-B. J. Chem. Soc., Perkin Trans. 1 1996, 2201. Lim, Y.-G.; Kang, J.-B.; Kim, Y.H. J. Chem. Soc., Chem. Commun. 1996, 585. Fujii, N.; Kakiuchi, F.; Chatani, N.; Murai, S. Chem. Lett. 1996, 939. Fujii, N.; Kakiuchi, F.; Yamada, A.; Chatani, N.; Murai, S. Chem. Lett. 1997, 425. See also refs .
25. For catalytic reaction involving cleavage of a C-H bond promoted by pyridine as a directing group, see: Lim, Y.-G.; Kim, Y.H.; Kang, J.-B. J. Chem. Soc., Chem. Commun. 1994, 2267. Lim, Y.-G.; Kim, Y.H.; Kang, J.-B. J. Chem. Soc., Perkin Trans. 1 1996, 2201. Lim, Y.-G.; Kang, J.-B.; Kim, Y.H. J. Chem. Soc., Chem. Commun. 1996, 585. Fujii, N.; Kakiuchi, F.; Chatani, N.; Murai, S. Chem. Lett. 1996, 939. Fujii, N.; Kakiuchi, F.; Yamada, A.; Chatani, N.; Murai, S. Chem. Lett. 1997, 425. See also refs .
26. For catalytic reaction involving cleavage of a C-H bond promoted by imine as a directing group, see: Kakiuchi, F.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1996, 111. See also ref .
27. Greene, T.W.; Wuts, P.G.M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley-Interscience: New York, 1991.
28. 12 (30 mg, 0.04 mmol), 1-acetyl-4-methylpiperazine (1a; 142 mg, 1 mmol), and toluene (3 mL). The autoclave was charged with ethylene to 10 atm and carbon monoxide to 15 atm at 25 °C, and then heated in an oil bath at 160 °C for 20 h. The autoclave was cooled and depressured. The solvent was removed in vacuo, and the coupling product was isolated by column chromatography on silica-gel with EtOAc/MeOH as eluant to give 140 mg (71%) of 1-(1-acetyl-4-methyl-1,4,5,6-tetrahydro-2-pyrazyl)-1-propanone (3a).
29. For papers on hydrogen transfer of dioxane to olefins, see: Nishiguchi, T.;Tachi, K.; Fukuzumi, K. J. Am. Chem. Soc. 1972, 94, 8916. Nishiguchi, T.; Fukuzumi, K. J. Am. Chem. Soc. 1974, 96, 1893. Masters, C.; Kiffen, A.A.; Visser, J.P. J. Am. Chem. Soc. 1976, 98, 1357. 1,4-Dimethylpiperazine was also used as a hydrogen donor in place of dioxane, albeit with low efficiency.
30. For papers on hydrogen transfer of dioxane to olefins, see: Nishiguchi, T.;Tachi, K.; Fukuzumi, K. J. Am. Chem. Soc. 1972, 94, 8916. Nishiguchi, T.; Fukuzumi, K. J. Am. Chem. Soc. 1974, 96, 1893. Masters, C.; Kiffen, A.A.; Visser, J.P. J. Am. Chem. Soc. 1976, 98, 1357. 1,4-Dimethylpiperazine was also used as a hydrogen donor in place of dioxane, albeit with low efficiency.
31. For papers on hydrogen transfer of dioxane to olefins, see: Nishiguchi, T.;Tachi, K.; Fukuzumi, K. J. Am. Chem. Soc. 1972, 94, 8916. Nishiguchi, T.; Fukuzumi, K. J. Am. Chem. Soc. 1974, 96, 1893. Masters, C.; Kiffen, A.A.; Visser, J.P. J. Am. Chem. Soc. 1976, 98, 1357. 1,4-Dimethylpiperazine was also used as a hydrogen donor in place of dioxane, albeit with low efficiency.
32. For a review on photoenolization/Diels-Alder reaction, see: Sammes, P.G. Tetrahedron 1976, 32, 405. See also, Senda, S.; Asao, T.; Sugiyama, I.; Hirota, K. Tetrahedron Lett. 1980, 21, 531.
33. For a review on photoenolization/Diels-Alder reaction, see: Sammes, P.G. Tetrahedron 1976, 32, 405. See also, Senda, S.; Asao, T.; Sugiyama, I.; Hirota, K. Tetrahedron Lett. 1980, 21, 531.