Enhanced catalyst activity and enantioselectivity with chirality-switchable polymer ligand PQXphos in Pd-catalyzed asymmetric silaborative cleavage of meso -methylenecyclopropanes

Journal of the American Chemical Society

Volumn 134, Issue 27, 2012, Pages 11092-11095

  Akai, Yuto ^a   Yamamoto, Takeshi ^a   Nagata, Yuuya ^a   Ohmura, Toshimichi ^a   Suginome, Michinori ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BINAPHTHYL; C-C BONDS; CHIRAL PHOSPHINE; DESYM-METRIZATION; HIGH ENANTIOSELECTIVITY; LOW-MOLECULAR WEIGHT; METHYLENECYCLOPROPANES; PALLADIUM-CATALYZED; POLYMER LIGANDS; RATE ENHANCEMENT;

CATALYSIS; ENANTIOSELECTIVITY; PHOSPHORUS COMPOUNDS; PROPANE;

LIGANDS;

CYCLOPROPANE DERIVATIVE; LEAD; LIGAND; PALLADIUM; PHOSPHINE DERIVATIVE; POLYMER;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONTROLLED STUDY; ENANTIOSELECTIVITY; MOLECULAR WEIGHT;

EID: 84863837244     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja303506k     Document Type: Article

References (37)

1. Lu, J.; Toy, P. H. Chem. Rev. 2009, 109, 815
2. Piguet, C.; Bernardinelli, G.; Hopfgartner, G. Chem. Rev. 1997, 97, 2005
3. Trindade, A. F.; Gois, P. M. P.; Afonso, C. A. M. Chem. Rev. 2009, 109, 418
4. Wang, Z.; Chen, G.; Ding, K. Chem. Rev. 2009, 109, 322
5. Benaglia, M.; Puglisi, A.; Cozzi, F. Chem. Rev. 2003, 103, 3401
6. Itsuno, S., Ed.; Polymeric Ciral Catalyst Design and Chiral Polymer Synthesis; Wiley: Weinheim, Germany, 2011.
7. Ding, K.; Uozumi, Y., Ed.; Handbook of Asymmetric Heterogeneous Catalysis; Wiley: Weinheim, Germany, 2008.
8. Reggelin, M.; Schultz, M.; Holbach, M. Angew. Chem., Int. Ed. 2002, 41, 1614
9. Reggelin, M.; Doerr, S.; Klussmann, M.; Schultz, M.; Holbach, M. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5461
10. Boersma, A. J.; Feringa, B. L.; Roelfes, G. Org. Lett. 2007, 9, 3647
11. Roelfes, G.; Feringa, B. L. Angew. Chem., Int. Ed. 2005, 44, 3230
12. Coquière, D.; Feringa, B.; Roelfes, G. Angew. Chem., Int. Ed. 2007, 46, 9308
13. Boersma, A. J.; Feringa, B. L.; Roelfes, G. Angew. Chem., Int. Ed. 2009, 48, 3346
14. Boersma, A. J.; Megens, R. P.; Feringa, B. L.; Roelfes, G. Chem. Soc. Rev. 2010, 39, 2083
15. Miyake, G. M.; Iida, H.; Hu, H.-Y.; Tang, Z.; Chen, E. Y. X.; Yashima, E. J. Polym. Sci. Polym. Chem. 2011, 49, 5192
16. Yashima, E.; Maeda, K.; Iida, H.; Furusho, Y.; Nagai, K. Chem. Rev. 2009, 109, 6102
17. Megens, R. P.; Roelfes, G. Chem.-Eur. J. 2011, 17, 8514
18. Ohta, H.; Tokunaga, M.; Obora, Y.; Iwai, T.; Iwasawa, T.; Fujihara, T.; Tsuji, Y. Org. Lett. 2007, 9, 89
19. Fujihara, T.; Tomike, Y.; Ohtake, T.; Terao, J.; Tsuji, Y. Chem. Commun. 2011, 47, 9699
20. Yamamoto, T.; Yamada, T.; Nagata, Y.; Suginome, M. J. Am. Chem. Soc. 2010, 132, 7899
21. Yamamoto, T.; Suginome, M. Angew. Chem., Int. Ed. 2009, 48, 539
22. Yamamoto, T.; Akai, Y.; Nagata, Y.; Suginome, M. Angew. Chem., Int. Ed. 2011, 50, 8844
23. Ito, Y.; Ihara, E.; Murakami, M.; Shiro, M. J. Am. Chem. Soc. 1990, 112, 6446
24. Ito, Y.; Ihara, E.; Murakami, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 1509
25. Ito, Y.; Ohara, T.; Shima, R.; Suginome, M. J. Am. Chem. Soc. 1996, 118, 9188
26. Ito, Y.; Miyake, T.; Hatano, S.; Shima, R.; Ohara, T.; Suginome, M. J. Am. Chem. Soc. 1998, 120, 11880
27. Suginome, M.; Collet, S.; Ito, Y. Org. Lett. 2002, 4, 351
28. Yamada, T.; Noguchi, H.; Nagata, Y.; Suginome, M. J. Polym. Sci., Part A 2010, 48, 898
29. Yamada, T.; Suginome, M. Macromolecules 2010, 43, 3999
30. Yamada, T.; Nagata, Y.; Suginome, M. Chem. Commun. 2010, 46, 4914
31. Significant enhancement of TON and TOF was achieved with polymer-based catalysts bearing PEG side chains in palladium-catalyzed allylic substitution reactions in water. Yamada, Y. M. A.; Sarkar, S. M.; Uozumi, Y. J. Am. Chem. Soc. 2012, 134, 3190
32. Ohmura, T.; Taniguchi, H.; Kondo, Y.; Suginome, M. J. Am. Chem. Soc. 2007, 129, 3518
33. Ohmura, T.; Taniguchi, H.; Suginome, M. Org. Lett. 2009, 11, 2880
34. Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015
35. Ohmura, T.; Suginome, M. Bull. Chem. Soc. Jpn. 2009, 82, 29
36. Hayashi, T.; Hirate, S.; Kitayama, K.; Tsuji, H.; Torii, A.; Uozumi, Y. Chem. Lett. 2000, 1272
37. Iwasawa, T.; Komano, T.; Tajima, A.; Tokunaga, M.; Obora, Y.; Fujihara, T.; Tsuji, Y. Organometallics 2006, 25, 4465