Development of chiral pincer palladium complexes bearing a pyrroloimidazolone unit. Catalytic use for asymmetric Michael addition

Organic Letters

Volumn 6, Issue 11, 2004, Pages 1833-1835

  Takenaka, Kazuhiro ^a   Uozumi, Yasuhiro ^a  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 PROPANOL; IMIDAZOLE DERIVATIVE; ISOPROPYL 2 CYANO 2 METHYL 5 OXOHEPTANOATE; KETONE DERIVATIVE; METHYL GROUP; PALLADIUM COMPLEX; PROPIONIC ACID DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; MICHAEL ADDITION; POLYMERIZATION; SYNTHESIS; X RAY ANALYSIS;

EID: 2942568460     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0494515     Document Type: Article

References (27)

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13. For recent catalytic synthetic applications with palladium pincer complexes, see: (a) Jung, I. G.; Son, S. U.; Park, K. H.; Chung, K.-C.; Lee, J. W.; Chung, Y. K. Organometallics 2003, 22, 4715. (b) Díez-Barra, E.; Guerra, J.; Hornillos, V.; Merino, S.; Tejeda, J. Organometallics 2003, 22, 4610. (c) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379. (d) Morales-Morales, D.; Redón, R.; Yung, C.; Jensen, C. M. Chem. Commun. 2000, 1619. (e) Ohff, M.; Ohff. A.; van der Boom, M. E.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687. (f) Bergbreiter, D. E.; Osburn, P. L.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531. (g) Gruber, A. S.; Zim, D.; Ebeling, G.; Monteiro, A. L.; Dupont, J. Org. Lett. 2000, 2, 1287. (h) Sjövall. S.; Wendt, O. F.; Andersson, C. J. Chem. Soc., Dalton Trans. 2002, 1396.
14. For recent catalytic synthetic applications with palladium pincer complexes, see: (a) Jung, I. G.; Son, S. U.; Park, K. H.; Chung, K.-C.; Lee, J. W.; Chung, Y. K. Organometallics 2003, 22, 4715. (b) Díez-Barra, E.; Guerra, J.; Hornillos, V.; Merino, S.; Tejeda, J. Organometallics 2003, 22, 4610. (c) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379. (d) Morales-Morales, D.; Redón, R.; Yung, C.; Jensen, C. M. Chem. Commun. 2000, 1619. (e) Ohff, M.; Ohff. A.; van der Boom, M. E.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687. (f) Bergbreiter, D. E.; Osburn, P. L.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531. (g) Gruber, A. S.; Zim, D.; Ebeling, G.; Monteiro, A. L.; Dupont, J. Org. Lett. 2000, 2, 1287. (h) Sjövall. S.; Wendt, O. F.; Andersson, C. J. Chem. Soc., Dalton Trans. 2002, 1396.
15. For recent catalytic synthetic applications with palladium pincer complexes, see: (a) Jung, I. G.; Son, S. U.; Park, K. H.; Chung, K.-C.; Lee, J. W.; Chung, Y. K. Organometallics 2003, 22, 4715. (b) Díez-Barra, E.; Guerra, J.; Hornillos, V.; Merino, S.; Tejeda, J. Organometallics 2003, 22, 4610. (c) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379. (d) Morales-Morales, D.; Redón, R.; Yung, C.; Jensen, C. M. Chem. Commun. 2000, 1619. (e) Ohff, M.; Ohff. A.; van der Boom, M. E.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687. (f) Bergbreiter, D. E.; Osburn, P. L.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531. (g) Gruber, A. S.; Zim, D.; Ebeling, G.; Monteiro, A. L.; Dupont, J. Org. Lett. 2000, 2, 1287. (h) Sjövall. S.; Wendt, O. F.; Andersson, C. J. Chem. Soc., Dalton Trans. 2002, 1396.
16. For recent catalytic synthetic applications with palladium pincer complexes, see: (a) Jung, I. G.; Son, S. U.; Park, K. H.; Chung, K.-C.; Lee, J. W.; Chung, Y. K. Organometallics 2003, 22, 4715. (b) Díez-Barra, E.; Guerra, J.; Hornillos, V.; Merino, S.; Tejeda, J. Organometallics 2003, 22, 4610. (c) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379. (d) Morales-Morales, D.; Redón, R.; Yung, C.; Jensen, C. M. Chem. Commun. 2000, 1619. (e) Ohff, M.; Ohff. A.; van der Boom, M. E.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687. (f) Bergbreiter, D. E.; Osburn, P. L.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531. (g) Gruber, A. S.; Zim, D.; Ebeling, G.; Monteiro, A. L.; Dupont, J. Org. Lett. 2000, 2, 1287. (h) Sjövall. S.; Wendt, O. F.; Andersson, C. J. Chem. Soc., Dalton Trans. 2002, 1396.
17. For recent catalytic synthetic applications with palladium pincer complexes, see: (a) Jung, I. G.; Son, S. U.; Park, K. H.; Chung, K.-C.; Lee, J. W.; Chung, Y. K. Organometallics 2003, 22, 4715. (b) Díez-Barra, E.; Guerra, J.; Hornillos, V.; Merino, S.; Tejeda, J. Organometallics 2003, 22, 4610. (c) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379. (d) Morales-Morales, D.; Redón, R.; Yung, C.; Jensen, C. M. Chem. Commun. 2000, 1619. (e) Ohff, M.; Ohff. A.; van der Boom, M. E.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687. (f) Bergbreiter, D. E.; Osburn, P. L.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531. (g) Gruber, A. S.; Zim, D.; Ebeling, G.; Monteiro, A. L.; Dupont, J. Org. Lett. 2000, 2, 1287. (h) Sjövall. S.; Wendt, O. F.; Andersson, C. J. Chem. Soc., Dalton Trans. 2002, 1396.
18. For recent catalytic synthetic applications with palladium pincer complexes, see: (a) Jung, I. G.; Son, S. U.; Park, K. H.; Chung, K.-C.; Lee, J. W.; Chung, Y. K. Organometallics 2003, 22, 4715. (b) Díez-Barra, E.; Guerra, J.; Hornillos, V.; Merino, S.; Tejeda, J. Organometallics 2003, 22, 4610. (c) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379. (d) Morales-Morales, D.; Redón, R.; Yung, C.; Jensen, C. M. Chem. Commun. 2000, 1619. (e) Ohff, M.; Ohff. A.; van der Boom, M. E.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687. (f) Bergbreiter, D. E.; Osburn, P. L.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531. (g) Gruber, A. S.; Zim, D.; Ebeling, G.; Monteiro, A. L.; Dupont, J. Org. Lett. 2000, 2, 1287. (h) Sjövall. S.; Wendt, O. F.; Andersson, C. J. Chem. Soc., Dalton Trans. 2002, 1396.
19. 3, Z = 4, R1 = 0.023, wR2 = 0.060, GOF = 0.94.
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21. For asymmetric Michael addition of α-cyanoesters with chiral transition metal catalysts, see: Rh complexes: (a) Sawamura, M.; Hamashima, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 8295. (b) Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron 1994, 50, 4439. (c) Inagaki, K.; Nozaki, K.; Takaya, H. Synlett 1997, 119. (d) Motoyama, Y.; Koga, Y.; Kobayashi, K.; Aoki, K.; Nishiyama, H. Chem. Eur. J. 2002, 8, 2968.
22. For asymmetric Michael addition of α-cyanoesters with chiral transition metal catalysts, see: Rh complexes: (a) Sawamura, M.; Hamashima, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 8295. (b) Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron 1994, 50, 4439. (c) Inagaki, K.; Nozaki, K.; Takaya, H. Synlett 1997, 119. (d) Motoyama, Y.; Koga, Y.; Kobayashi, K.; Aoki, K.; Nishiyama, H. Chem. Eur. J. 2002, 8, 2968.
23. For asymmetric Michael addition of α-cyanoesters with chiral transition metal catalysts, see: Rh complexes: (a) Sawamura, M.; Hamashima, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 8295. (b) Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron 1994, 50, 4439. (c) Inagaki, K.; Nozaki, K.; Takaya, H. Synlett 1997, 119. (d) Motoyama, Y.; Koga, Y.; Kobayashi, K.; Aoki, K.; Nishiyama, H. Chem. Eur. J. 2002, 8, 2968.
24. For asymmetric Michael addition of α-cyanoesters with chiral transition metal catalysts, see: Rh complexes: (a) Sawamura, M.; Hamashima, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 8295. (b) Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron 1994, 50, 4439. (c) Inagaki, K.; Nozaki, K.; Takaya, H. Synlett 1997, 119. (d) Motoyama, Y.; Koga, Y.; Kobayashi, K.; Aoki, K.; Nishiyama, H. Chem. Eur. J. 2002, 8, 2968.
25. Pt complexes: (e) Blacker, A. J.; Clarke, M. L.; Loft, M. S.; Mahon, M. F.; Williams, J. M. J. Organometallics 1999, 18, 2867.
26. Pd complexes: (f) Stark, M. A.; Jones, G.; Richards, C. J. Organometallics 2000, 19, 1282.
27. See: Handbook of Organopalladium Chemistry; Negishi, E., Ed.; Wiley: New York, 2002.