Erratum: Highly active and enantioselective rhodium-catalyzed asymmetric 1,4-addition of arylboronic acid to α,β-unsaturated ketone by using Electron-Poor MeO-F12-BIPHEP (Advanced Synthesis and Catalysis (2010) 18 (3247-3254) DOI 10.1002/adsc.201000339);Highly active and enantioselective rhodium-catalyzed asymmetric 1,4-addition of arylboronic acid to α,β-unsaturated ketone by using electron-poor MeO-F12-BIPHEP

Advanced Synthesis and Catalysis

Volumn 352, Issue 18, 2010, Pages 3247-3254

  Korenaga, Toshinobu ^a   Maenishi, Ryota ^a   Hayashi, Keigo ^a   Sakai, Takashi ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

asymmetric catalysis; density function theory (DFT) calculations; fluorinated ligands; phosphane ligands; rhodium

Indexed keywords

EID: 78650387767     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201190014     Document Type: Erratum

References (36)

1. Reviews
2. M. Miyaura, Bull. Chem. Soc. Jpn. 2008, 81, 1535-1553
3. T. Hayashi, K. Yamasaki, Chem. Rev. 2003, 103, 2829-2844.
4. S. Brock, D. R. J. Hose, J. D. Moseley, A. J. Parker, I. Patel, A. J. Williams, Org. Process Res. Dev. 2008, 12, 496-502.
5. Y. Takaya, M. Ogasawara, T. Hayashi, Tetrahedron Lett. 1999, 40, 6957-6961
6. R. Amengual, V. Michelet, J.-P. Genêt, Synlett 2002, 1791-1794
7. M. Pucheault, S. Darses, J.-P. Genêt, Eur. J. Org. Chem. 2002, 3552-3557
8. J.-G. Boiteau, A. J. Minnaard, B. L. Feringa, J. Org. Chem. 2003, 68, 9481-9484
9. F.-X. Chen, A. Kina, T. Hayashi, Org. Lett. 2006, 8, 341-344
10. T. Korenaga, K. Osaki, R. Maenishi, T. Sakai, Org. Lett. 2009, 11, 2325-2328.
11. S. Jeulin, S. Duprat de Paule, V. Ratovelomanana-Vidal, J.-P. Genêt, N. Champion, P. Dellis, Angew. Chem. 2004, 116, 324-329
12. Angew. Chem. Int. Ed. 2004, 43, 320-325
13. K. Mashima, K. Kusano, N. Saito, Y. Matsumura, K. Nozaki, H. Kumobayashi, N. Sayo, Y. Hori, T. Ishizaki, S. Akutagawa, H. Takaya, J. Org. Chem. 1994, 59, 3064-3076.
14. T. Hayashi, M. Takahashi, Y. Takaya, M. Ogasawara, J. Am. Chem. Soc. 2002, 124, 5052-5058.
15. A. Kina, H. Iwamura, T. Hayashi, J. Am. Chem. Soc. 2006, 128, 3904-3905.
16. K. A. Bunten, D. H. Farrar, A. J. Poë, A. Lough, Organometallics 2002, 21, 3344-3350.
17. G. Aullõn, G. Ujaque, A. Lledõs, S. Alvarez, S. P. Alemany, Inorg. Chem. 1998, 37, 804-813.
18. R. Itooka, Y. Iguchi, N. Miyaura, J. Org. Chem. 2003, 68, 6000-6004.
19. Instability of the M-P bond of fluorinated aryl phosphane as compared to arylphosphane:, C. L. Pollock, G. C. Saunders, E. C. M. S. Smyth, V. I. Sorokin, J. Fluorine Chem. 2008, 129, 142-166.
20. Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, N. Miyaura, J. Am. Chem. Soc. 1998, 120, 5579-5580.
21. M. L. Clarke, M. Heydt, Organometallics 2005, 24, 6475-6478.
22. Q. Chen, B.-L. Lin, Y. Fu, L. Liu, Q.-X. Guo, Res. Chem. Intermed. 2005, 31, 759-767.
23. [3b]
24. -1)
25. -1)
26. -1)
27. -1)
28. -1)
29. A. Lei, M. He, S. Wu, X. Zhang, Angew. Chem. 2002, 114, 3607-3610
30. -1).
31. H. Buschmann, H. D. Scharf, N. Hoffmann, P. Esser, Angew. Chem. 1991, 103, 480-518
32. Angew. Chem. Int. Ed. Engl. 1991, 30, 477-515.
33. [3d]
34. [19] The 6-31G(d) basis set was applied to all elements except Rh, which was described with the LANL2DZ effective core potential and the LANL2DZ basis set. All the geometries are analyzed by harmonic vibrational frequencies obtained at the same level and characterized as a transition state (one imaginary frequency). IRC calculations were performed to confirm C-C bond formation between Ph and 2a.
35. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, Gaussian 03, Revision E.01, Gaussian, Inc., Wallingford, CT, 2004.
36. T. Korenaga, R. Maenishi, K. Osaki, T. Sakai, Heterocycles 2010, 80, 157-162.