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Developing asymmetric iron and ruthenium-based cyclone complexes : complex factors influence the asymmetric induction in the transfer hydrogenation of ketones

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Hopewell, Jonathan P., Martins, José E. D., Johnson, Tarn C., Godfrey, Jamie and Wills, Martin. (2012) Developing asymmetric iron and ruthenium-based cyclone complexes : complex factors influence the asymmetric induction in the transfer hydrogenation of ketones. Organic & Biomolecular Chemistry, Vol.10 (No.1). pp. 134-145. ISSN 1477-0520

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Official URL: http://dx.doi.org/10.1039/C1OB06010D

Abstract

The preparation of a range of asymmetric iron and ruthenium-cyclone complexes, and their application to the asymmetric reduction of a ketone, are described. The enantioselectivity of ketone reduction is influenced by a single chiral centre in the catalyst, as well as by the planar chirality in the catalyst. This represents the first example of asymmetric ketone reduction using an iron cyclone catalyst.

Item Type:

Journal Article

Subjects:

Q Science > QD Chemistry

Divisions:

Faculty of Science > Chemistry

Library of Congress Subject Headings (LCSH):

Asymmetric synthesis, Ketones, Iron, Ruthenium

Journal or Publication Title:

Organic & Biomolecular Chemistry

Publisher:

Royal Society of Chemistry

ISSN:

1477-0520

Official Date:

2012

Dates:

Date	Event
2012	Published

Volume:

Vol.10

Number:

No.1

Page Range:

pp. 134-145

Identification Number:

10.1039/c1ob06010d

Status:

Peer Reviewed

Publication Status:

Published

Access rights to Published version:

Restricted or Subscription Access

Funder:

Engineering and Physical Sciences Research Council (EPSRC), University of Warwick

Grant number:

EP/F019424 (EPSRC), EP/G01244X/1 (EPSRC)

References:

1) (a) B. L. Conley, M. K. Pennington-Boggio, E. Boz and T. J. Williams, Chem. Rev. 2010, 110, 2294-2312. (b) Y. Blum, Y. Shvo, J. Organomet. Chem. 1985, 282, C7-C10. (c) Y. Shvo, D. Czarkie and Y. Rahamim, J. Am. Chem. Soc. 1986, 108, 7400-7402..
2) (a) O. Pàmies and J.-E. Bäckvall, Chem. Rev., 2003, 103, 3247-3262. (b) B. A. Persson, A. I. E. Larsson, M. Le Ray, J.-E. Bäckvall, J. Am. Chem. Soc. 1999, 121, 1645-1650. (c) O. Pamies, J.-E. Bäckvall, J. Org. Chem. 2001, 66, 4022-4025.
3) (a) L. K. Thalén, D. Zhao, J.-B. Sortais, J. Paetzold, C. Hoben, J.-E. Bäckwall, Angew. Chem. Int. Edn. 2009, 15, 3403-3410. (b) J. S. M. Samec, J.-E. Bäckvall, Chem. Eur. J. 2002, 8, 2955-2961. (c) J. Paetzold, J.-E. Bäckwall, J. Am. Chem. Soc. 2005, 127, 17620-17621.
4) (a) J. S. M. Samec, J.-E. Bäckvall, P. G. Andersson and P. Brandt, Chem. Soc. Rev. 2006, 35, 237-248. (b) S. E. Clapham, A Hadzovic and R. H. Morris, Coord. Chem. Rev. 2004, 248, 2201-2237. (c) C. P. Casey, S. W. Singer, D. R. Powell, R. K. Hayashi, M. Kavana, J. Am. Chem. Soc. 2001, 123, 1090-1100. (d) J. B. Johnson, J.-E. Bäckvall, J. Org. Chem. 2003, 68, 7681-7684. (e) Comas-Vives, G. Ujaque, A. Lledós, Organometallics, 2007, 26, 4135-4144. (f) C. P. Casey, S. E. Beetner, J. B. Johnson, J. Am. Chem. Soc. 2008, 130, 2285-2295.
5) (a) M. Yamakawa, I. Yamada, R. Noyori, Angew. Chem., Int. Ed. 2001, 40, 2818-2821. (b) C. P. Casey, J. B. Johnson, J. Org. Chem. 2003, 68, 1998-2001. (c) S. Hashiguchi, A. Fujii, K. J. Haack, K. Matsumura, T. Ikariya and R. Noyori, Angew. Chem. Int. Edn. 1997, 36, 288-290. (d) F. K. Cheung, C. Lin, F. Minissi, A. Lorente Crivillé, M. A. Graham, D. J. Fox, M. Wills, Org. Lett. 2007, 9, 4659-4662. (e) A. M. Hayes, D. J. Morris, G. J. Clarkson, M. Wills, J. Am. Chem. Soc. 2005, 127, 7318-7319.
6) C. P. Casey, T. E. Vos, S. W. Singer, H. A. Guzel, J. Org. Chem. 2002, 21, 5038-5046.
7) (a) H.–J. Knölker, E. Baum, H. Goesmann and R. Klauss, Angew. Chem. Int. Edn. 1999, 38, 2064-2066. (b) H. H. Zhang, D. Z. Chen, Y. H. Zhang, G. Q. Zhang and J. B. Liu, Dalton Transactions 2010, 39, 1972-1978. (c) G. N. Schrauzer, J. Am. Chem. Soc. 1959, 81, 5307-5310.
8) (a) C. P. Casey and H. Guan, J. Am. Chem. Soc. 2007, 129, 5816-5817. (b) C. P. Casey and H. Guan, J. Am. Chem. Soc. 2009, 131, 2499-2507. (c) H. Zhang, D. Chen, Y. Zhang, G. Zhang and J. Liu, Dalton Trans. 2010, 39, 1972-1978
9) (a) M. G. Coleman, A. N. Brown, B. A. Bolton and H. Guan, Adv. Synth. Catal. 2010, 352, 967-970. (b) S. A. Moyer and T. W. Funk, Tetrahedron Lett. 2010, 51, 5430-5433. (c) M. K. Thorson, K. L. Klinkel, J. Wang and T. J. Williams, Eur. J. Inorg. Chem. 2009, 295-302.
10) T. C. Johnson, G. J. Clarkson and M. Wills, Organometallics 2011, 30, 1859-1868.
11) (a) A. J. Pearson and R. J. Shively Jr., Organometallics, 1992, 11, 4096-4104. (b) A. J. Pearson and R. J. Shively Jr., Organometallics, 1994, 13, 578-584.
12) (a) Y. Yamamoto, K. Yamashita and M. Nakamura, Organometallics 2010, 29, 1472-1478. (b) A. Berkessel, S. Reichau, A. van der Höh, 5 N. Leconte and J.-M. Neudörfl, Organometallics 2011, 30, 3880-3887.
13) (a) N. A. Bailey, V. S. Jassal, R. Vefghi and C. White, J. Chem. Soc. Dalton Trans. 1987, 2815-2822. (b) J. H. Eekhof, H. Hogeveen and R. M. Kellogg, Chem. Commun. 1977, 705. (c) H.–J. Knölker, E. Baum and J. Heber, Tetrahedron Lett. 1992, 36, 7647-7650.
14) (a) K. Matsumura, S. Hashiguchi, T. Ikariya and R. Noyori, J. Am. Chem. Soc. 1997, 119, 8738-8739. (b) D. J. Morris, A. M. Hayes and M. Wills, J. Org. Chem. 2006, 71, 7035-7044. (c) J. A. Marshall. P Eidam and H. S. Eidam, J. Org. Chem. 2006, 71, 4840-4844.
15) Y. Yamamoto, Y. Miyabe and K.Itoh, Eur. J. Inorg. Chem. 2004, 3651-3661.
16) O. Hamed, P. M. Henry and D. P. Becker, Tetrahedron Lett. 2010, 51, 3514-3517.
17) M. M. Midland, A. Tramontano, A. Kazubski, R. S. Graham, D. J. S. Tsai and D. B. Cardin, Tetrahedron 1984, 40, 1371-1380. (R)-Alpine borane is derived from (+)--pinene and gives the (R)-reduction product illustrated.
18) (a) G. Bauer and K. A. Kirchner, Angew. Chem. Int. Ed. 2011, 50, 5798-5800. (b) A. Naik, T. Maji and O. Reiser, Chem. Commun. 2010, 46, 4475–4477. (c) R.H. Morris, Chem. Soc. Rev. 2009, 38, 2282–2291. (d) S. Enthaler, K. Junge and M. Beller, Angew. Chem. Int. Ed. 2008, 47, 3317-3321. (e) C. Sui-Seng, F. Freutel, A. J. Lough and R. H. Morris, Angew. Chem. Int. Ed. 2008, 47, 940-943. (f) A. Mikhailine, A. J. Lough and R. H. Morris, J. Am. Chem. Soc. 2009, 131, 1394–1395. (g) N. Meyer, A. J. Lough and R. H. Morris, Chem. Eur. J. 2009, 15, 5605-5610. (h) J.-S. Chen, L.-L. Chen, Y. Xing, G. Chen, W.-Y. Shen, Z.-R. Dong, Y.-Y. Li and J.-X. Gao, Acta. Chim. Sin. (Huaxue Xuebao) 2004, 62, 1745-1750. (i) S. Zhou, S. Fleischer, K. Junge, S. Das, D. Addis and M. Beller, Angew. Chem. Int. Ed. 2010, 49, 8121-8125. (j) A. A. Mikhailine and R. H. Morris, Inorg. Chem. 2010, 49, 11039–11044. (k) P. O. Lagaditis, A. J. Lough, and R. H. Morris Inorg. Chem. 2010, 49, 10057–10066. (l) K. Junge, K. Schroder and M. Beller, Chem. Commun. 2011, 4849-4859. (m) S. Zhou, S. Fleischer, K. Junge and M. Beller, Angew. Chem. Int. Ed. 2011, 50, 5120-5124.
19) C. J. Taylor, M. Motevalli, and C. J. Richards, Organometallics, 2006, 25, 2899–2902.
20) T. Schubert, W. Hummel, M.-R. Kula and M. Müller, Eur. J. Org. Chem. 2001, 4181-4187
21) L. Xu, M. R. Muller, X. Yu and B.-Q. Zhu, Synth. Commun. 2009, 39, 1611-1625.