ACS Catalysis
Research Article
Organometallics 2010, 29, 5791−5804. (g) Arribas, I.; Rubio, M.;
Kleman, P.; Pizzano, A. J. Org. Chem. 2013, 78, 3997−4005.
(31) The N-phthalimido fragment has shown to be an effective
auxiliary group in asymmetric hydrogenation reactions. For examples,
see: (a) Wang, C.-J.; Sun, X.; Zhang, X. Angew. Chem., Int. Ed. 2005,
44, 4933−4935. (b) Huang, H.; Liu, X.; Deng, J.; Qiu, M.; Zheng, Z.
Org. Lett. 2006, 8, 3359−3362. (c) Yang, Q.; Gao, W.; Deng, J.; Zhang,
X. Tetrahedron Lett. 2006, 47, 821−823. (d) Deng, J.; Duan, Z.-C.;
Huang, J.-D.; Hu, X.-P.; Wang, D.-Y.; Yu, S.-B.; Xu, X.-F.; Zheng, Z.
Org. Lett. 2007, 9, 4825−4828. (e) Chen, J.; Liu, Q.; Zhang, W.;
Spinella, S.; Lei, A.; Zhang, X. Org. Lett. 2008, 10, 3033−3036.
(32) Gridnev, I. D.; Imamoto, T. Chem. Commun. 2009, 7447−7464.
(33) (a) Kim, K. H.; Ishikawa, K.; Takezoe, H.; Fukuda, A. Phys. Rev.
E 1995, 51, 2166−2175. (b) Fergusson, K. M.; Hird, M. Adv. Mater.
2007, 19, 211−214. (c) Zhang, Y.; Martinez-Perdiguero, J.;
Baumeister, U.; Walker, C.; Etxebarria, J.; Prehm, M.; Ortega, J.;
Tschierske, C.; O’Callaghan, M.J.; Harant, A.; Handschy, M. J. Am.
Chem. Soc. 2009, 131, 18386−18392.
́
(18) Kleman, P.; Gonzalez-Liste, P. J.; García-Garrido, S. E.;
Cadierno, V.; Pizzano, A. Chem.Eur. J. 2013, 19, 16209−16212.
(19) (a) Goossen, L. J.; Paetzold, J.; Koley, D. Chem. Commun. 2003,
706−707. (b) Cadierno, V.; Francos, J.; Gimeno, J. Organometallics
2011, 30, 852−862. (c) Nicks, F.; Libert, L.; Delaude, L.; Demonceau,
A. Aust. J. Chem. 2009, 62, 227−231.
(20) Chary, B. C.; Kim, S. J. Org. Chem. 2010, 75, 7928−7931.
(21) The lower enantioselectivity observed at higher pressure
matches the behavior originally described by Halpernin with respect
to the hydrogenation of methyl Z-α-acetamidocinnamate with Rh
cationic catalysts (ref 22a). However, a comprehensive study described
by Bellefon have shown variations of ee with pressure in this reaction
in either direction depending on the nature of the chiral ligand (ref
22b).
(34) (a) Lee, H.-K.; Doi, K.; Harada, H.; Tsutsumi, O.; Kanazawa, A.;
Shiono, T.; Ikeda, T. J. Phys. Chem. B 2000, 104, 7023−7028.
(b) Iamsaard, S.; Aßhoff, S. J.; Matt, B.; Kudernac, T.; Cornelissen, J.
L. M.; Fletcher, S. P.; Katsonis, N. Nat. Chem. 2014, 6, 229−235.
(35) (a) Yan, Y.-Y.; RajanBabu, T. V. Org. Lett. 2000, 2, 4137−4140.
(b) Wang, F.; Wang, H.; Polavarapu, P. L.; Rizzo, C. J. J. Org. Chem.
2001, 66, 3507−3512. (c) Martín-Zamora, E.; Ferrete, A.; Llera, J. M.;
(22) For studies dealing with the dependence of enantioselectivity
with pressure for Rh-catalyzed olefin hydrogenation, see: (a) Landis,
C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746−1754. (b) Alame,
M.; Pestre, N.; de Bellefon, C. Adv. Synth. Catal. 2008, 350, 898−908.
(c) Schmidt, T.; Dai, Z.; Drexler, H.-J.; Hapke, M.; Preetz, A.; Heller,
D. Chem.Asian J. 2008, 3, 1170−1180.
(23) (a) Arnone, A.; Bravo, P.; Panzeri, W.; Viani, F.; Zanda, M. Eur.
J. Org. Chem. 1999, 117−127. (b) Nakamura, Y.; Mori, K. Eur. J. Org.
Chem. 1999, 2175−2182. (c) Kobayashi, Y.; Fukuda, A.; Kimachi, T.;
Ju-ichi, M.; Takemoto, Y. Tetrahedron 2005, 61, 2607−2622.
(24) (a) Taylor, K. M.; Snyder, S. H. Science 1970, 168, 1487−1489.
(b) Sano, M.; Ernesto, C.; Thomas, R. G.; Klauber, M. R.; Schafer, K.;
Grundman, M.; Woodbury, P.; Growdon, J.; Cotman, C. W.; Pfeiffer,
E.; Schneider, L. S.; Thal, L. J. N. Eng. J. Med. 1997, 336, 1216−1222.
(c) Talluri, S. K.; Sudalai, A. Tetrahedron 2007, 63, 9758−9763.
(25) (a) Nacsa, E. D.; Lambert, T. H. Org. Lett. 2012, 15, 38−41.
(b) Zhang, J.; Wang, H.; Ma, Y.; Wang, Y.; Zhou, Z.; Tang, C.
Tetrahedron Lett. 2013, 54, 2261−2263.
́
Munoz, J. M.; Pappalardo, R. R.; Fernandez, R.; Lassaletta, J. M.
̃
Chem.Eur. J. 2004, 10, 6111−6129. (d) Holz, J.; Zayas, O.; Jiao, H.;
Baumann, W.; Spannenberg, A.; Monsees, A.; Riermeier, T. H.;
Almena, J.; Kadyrov, R.; Boerner, A. Chem.Eur. J. 2006, 12, 5001−
5013. (e) Bonnaventure, I.; Charette, A. B. J. Org. Chem. 2008, 73,
6330−6340. (f) Tartaglia, S.; Pace, F.; Scafato, P.; Rosini, C. Org. Lett.
2008, 10, 3421−3424. (g) Pungaliya, C.; Srinivasan, J.; Fox, B. W.;
Malik, R. U.; Ludewig, A. H.; Sternberg, P. W.; Schroeder, F. C. Proc.
Natl. Acad. Sci. U.S.A. 2009, 106, 7708−7713. (h) Kelly, B. D.;
Lambert, T. H. Org. Lett. 2011, 13, 740−743. (i) Suzuki, Y.;
Wakatsuki, J.; Tsubaki, M.; Sato, M. Tetrahedron 2013, 69, 9690−
9700.
(26) (a) Mastalerz, H.; Chang, M.; Chen, P.; Dextraze, P.; Fink, B. E.;
Gavai, A.; Goyal, B.; Han, W.-C.; Johnson, W.; Langley, D.; Lee, F. Y.;
Marathe, P.; Mathur, A.; Oppenheimer, S.; Ruediger, E.; Tarrant, J.;
Tokarski, J. S.; Vite, G. D.; Vyas, D. M.; Wong, H.; Wong, T. W.;
Zhang, H.; Zhang, G. Bioorg. Med. Chem. Lett. 2007, 17, 2036−2042.
(b) Thiel, O. R.; Bernard, C.; King, T.; Dilmeghani-Seran, M.; Bostick,
T.; Larsen, R. D.; Faul, M. M. J. Org. Chem. 2008, 73, 3508−3515.
(c) Singer, J. M.; Wilson, M. W.; Johnson, P. D.; Graham, S. R.;
Cooke, L. W.; Roof, R. L.; Boxer, P. A.; Gold, L. H.; Meltzer, L. T.;
Janssen, A.; Roush, N.; Campbell, J. E.; Su, T.-Z.; Hurst, S. I.; Stoner,
C. L.; Schwarz, J. B. Bioorg. Med. Chem. Lett. 2009, 19, 2409−2412.
(d) Bagutski, V.; French, R. M.; Aggarwal, V. K. Angew. Chem., Int. Ed.
2010, 49, 5142−5145. (e) Sindac, J. A.; Yestrepsky, B. D.; Barraza, S.
J.; Bolduc, K. L.; Blakely, P. K.; Keep, R. F.; Irani, D. N.; Miller, D. J.;
(36) (a) Katzberg, M.; Wechler, K.; Muller, M.; Dunkelmann, P.;
Stohrer, J.; Hummel, W.; Bertau, M. Org. Biomol. Chem. 2009, 7, 304−
314. (b) Muller, M.; Katzberg, M.; Bertau, M.; Hummel, W. Org.
Biomol. Chem. 2010, 8, 1540−1550.
(37) Martín-Matute, B.; Edin, M.; Backvall, J.-E. Chem.Eur. J. 2006,
̈
12, 6053−6061.
́
(38) (a) Leijondahl, K.; Boren, L.; Braun, R.; Backvall, J.-E. Org. Lett.
̈
2008, 10, 2027−2030. (b) Leijondahl, K.; Boren
́
, L. A.; Braun, R.;
Backvall, J.-E. J. Org. Chem. 2009, 74, 1988−1993.
̈
(39) (a) Dyck, L. E.; Durden, D. A.; Boulton, A. A. J. Neurochem.
1986, 46, 399−404. (b) Harbeson, S. L.; Tung, R. D. In Annuual
Reports in Medicinal Chemistry; Macor, J. E., Ed.; Elsevier: The
Netherlands, 2011; Vol. 46, pp 403−417. (c) Neubert, L.; Michalik,
D.; Bahn, S.; Imm, S.; Neumann, H.; Atzrodt, J.; Derdau, V.; Holla,
̈
W.; Beller, M. J. Am. Chem. Soc. 2012, 134, 12239−12244.
Larsen, S. D. J. Med. Chem. 2012, 55, 3535−3545. (f) Karlstrom, S.;
̈
(d) Katsnelson, A. Nat. Med. 2013, 19, 656−656.
Nordvall, G.; Sohn, D.; Hettman, A.; Turek, D.; Åhlin, K.; Kers, A.;
Claesson, M.; Slivo, C.; Lo-Alfredsson, Y.; Petersson, C.; Bessidskaia,
G.; Svensson, P. H.; Rein, T.; Jerning, E.; Malmberg, Å.; Ahlgen, C.;
Ray, C.; Vares, L.; Ivanov, V.; Johansson, R. J. Med. Chem. 2013, 56,
3177−3190.
(40) (a) Sheldon, R. A. Green Chem. 2005, 7, 267−278. (b) Sheldon,
R. A. Chem. Commun. 2008, 3352−3365. (c) Walsh, P. J.; Li, H.; de
Parrodi, C. A. Chem. Rev. 2007, 107, 2503−2545. (d) Dach, R.; Song,
J. J.; Roschangar, F.; Samstag, W.; Senanayake, C. H. Org. Process Res.
Dev. 2012, 16, 1697−1706.
(27) (a) Nakazato, A.; Sakagami, K.; Yasuhara, A.; Ohta, H.;
Yoshikawa, R.; Itoh, M.; Nakamura, M.; Chaki, S. J. Med. Chem. 2004,
47, 4570−4587. (b) Li, L.; Beaulieu, C.; Carriere, M.-C.; Denis, D.;
Greig, G.; Guay, D.; O’Neill, G.; Zamboni, R.; Wang, Z. Bioorg. Med.
Chem. Lett. 2010, 20, 7462−7465.
(41) (a) Heller, D.; Drexler, H.-J.; Spannenberg, A.; Heller, B.; You,
J.; Baumann, W. Angew. Chem., Int. Ed. 2002, 41, 777−780. (b) Fischer,
C.; Thede, R.; Drexler, H.-J.; Konig, A.; Baumann, W.; Heller, D.
̈
Chem.Eur. J. 2012, 18, 11920−11928.
(42) For another application of asymmetric hydrogenation
performed at high substrate concentration, see: Hoge, G.; Wu, H.-
P.; Kissel, W. S.; Pflum, D. A.; Greene, D. J.; Bao, J. J. Am. Chem. Soc.
2004, 126, 5966−5967.
(28) It should also be noted that limiting the influence of the
cyclopropyl substituent to its steric effects may be an oversimplified
interpretation due to the electronic properties of this group. For a
review on this topic, see: de Meijere, A. Angew. Chem., Int. Ed. 1979,
18, 809−826.
(43) Vargas, S.; Rubio, M.; Suarez, A.; del Rio, D.; Alvarez, E.;
Pizzano, A. Organometallics 2006, 25, 961−973.
(29) Imamoto, T.; Itoh, T.; Yoshida, K.; Gridnev, I. D. Chem.Asian
J. 2008, 3, 1636−1641.
(30) Gupta, P.; Shah, B. A.; Parshad, R.; Qazi, G. N.; Taneja, S. C.
Green Chem. 2007, 9, 1120−1125.
4408
dx.doi.org/10.1021/cs501402z | ACS Catal. 2014, 4, 4398−4408