F. Chen et al. / Tetrahedron 68 (2012) 5248e5257
5257
see: (c) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem.
Soc. 1995, 117, 7562e7563; (d) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.;
Noyori, R. J. Am. Chem. Soc. 1995, 118, 2521e2522; (e) Uematsu, N.; Fujii, A.;
Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 4916e4917.
12. For pioneering work on using chiral metal complexes of diamine for
asymmetric hydrogenation of ketones, see: (a) Ito, M.; Hirakawa, M.; Mur-
ata, K.; Ikariya, T. Organometallics 2001, 20, 379e381; (b) Ohkuma, T.; Ut-
sumi, N.; Tsutsumi, K.; Murata, K.; Sandoval, C.; Noyori, R. J. Am. Chem. Soc.
2006, 128, 8724e8725 For other examples, see: (c) Ohkuma, T.; Tsutsumi,
K.; Utsumi, N.; Arai, N.; Noyori, R.; Murata, K. Org. Lett. 2007, 9, 255e257;
(d) Ohkuma, T.; Utsumi, N.; Watanabe, M.; Tsutsumi, K.; Arai, N.; Murata, K.
Org. Lett. 2007, 9, 2565e2567; (e) Ito, M.; Endo, Y.; Ikariya, T. Organome-
tallics 2008, 27, 6053e6055; (f) Touge, T.; Hakamata, T.; Nara, H.; Kobayashi,
T.; Sayo, N.; Saito, T.; Kayaki, Y.; Ikariya, T. J. Am. Chem. Soc. 2011, 133,
14960e14963.
13. For asymmetric hydrogenation of quinolines, quinoxalines, and imines with
chiral metal complexes of diamine from our group’s work, see: (a) Wang, T.;
Zhuo, L.; Li, Z.; Chen, F.; Ding, Z.; He, Y.; Fan, Q.-H.; Xiang, J.; Yu, Z.-X.; Chan, A.
S. C. J. Am. Chem. Soc. 2011, 133, 9878e9891; (b) Zhou, H.; Li, Z.; Wang, Z.; Wang,
T.; Xu, L.; He, Y.; Fan, Q.-H.; Pan, J.; Gu, L.; Chan, A. S. C. Angew. Chem., Int. Ed.
2008, 47, 8464e8467; (c) Li, Z.; Wang, T.; He, Y.; Wang, Z.; Fan, Q.-H.; Pan, J.; Xu,
L. Org. Lett. 2008, 10, 5265e5268; (d) Wang, Z.; Zhou, H.; Wang, T.; He, Y.; Fan,
Q.-H. Green Chem. 2009, 11, 767e769; (e) Wang, T.; Ouyang, G.; He, Y.; Fan, Q.-H.
Synlett 2011, 939e942; (f) Qin, J.; Chen, F.; Ding, Z.; He, Y.; Xu, L.; Fan, Q.-H. Org.
Lett. 2011, 13, 6568e6571; (g) Chen, F.; Wang, T.; He, Y.; Ding, Z.; Li, Z.; Xu, L.;
Fan, Q.-H. Chem.dEur. J. 2011, 17, 1109e1113; (h) Chen, F.; Ding, Z.; Qin, J.; Wang,
T.; He, Y.; Fan, Q.-H. Org. Lett. 2011, 13, 4348e4351; (i) Chen, F.; Li, Z.; He, Y.; Fan,
Q.-H. Chin. J. Chem. 2010, 28, 1529e1532; (j) He, Y.; Fan, Q.-H. Org. Biomol. Chem.
2010, 8, 2497e2504.
14. For asymmetric hydrogenation of imines with chiral metal complexes of di-
amine from other groups’ work, see: (a) Li, C.; Xiao, J. J. Am. Chem. Soc. 2008,
130, 13208e13209; (b) Li, C.; Wang, C.; Villa-Marcos, B.; Xiao, J. J. Am. Chem. Soc.
2008, 130, 14450e14451; (c) Li, C.; Villa-Marcos, B.; Xiao, J. J. Am. Chem. Soc.
2009, 131, 6967e6969; (d) Cheruku, P.; Church, T. L.; Andersson, P. G. Chem.
dAsian J. 2008, 3, 1390e1394; (e) Shirai, S.-Y.; Nara, H.; Kayaki, Y.; Ikariya, T.
Organometallics 2009, 28, 802e809.
15. The first example of asymmetric hydrogenation of N-alkyl imines catalyzed by
Rhediphosphine complex, see: Levi, A.; Modena, G.; Scorrano, G. J. Chem. Soc.,
Chem. Commun. 1975, 6e7.
16. Hansen, K. B.; Rosner, T.; Kubryk, M.; Dormer, P. G.; Armstrong, J. D. Org. Lett.
2005, 7, 4935e4938.
17. For reviews, see: (a) Lacour, J.; Hebbe-Viton, V. Chem. Soc. Rev. 2003, 32,
373e382; (b) Macchioni, A. Chem. Rev. 2005, 105, 2039e2074; (c) Lacour, J.;
Moraleda, D. Chem. Commun. 2009, 7073e7089; (d) Rueping, M.; Koenigs, R. M.;
Atodiresei, I. Chem.dEur. J. 2010, 16, 9350e9365.
References and notes
1. (a) Blaser, H.-U.; Malan, C.; Pugin, B.; Spinder, F.; Steiner, H.; Studer, M. Adv.
Synth. Catal. 2003, 345, 103e151; (b) Chiral Amine Synthesis: Methods, De-
velopments and Applications; Nugent, T. C., Ed.; Wiley-VCH: Weinheim, 2010.
2. For selected recent reviews on asymmetric hydrogenation of imines, see: (a)
Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029e3069; (b) Spindler, F.; Blaser,
H.-U. In; de Vries, J. G., Elsevier, C. J., Eds. Handbook of Homogeneous Hydro-
genation; Wiley-VCH: Weinheim, 2007; Vol. 1, pp 1193e1214; (c) Nugent, T. C.;
ꢀ
El-Shazly, M. Adv. Synth. Catal. 2010, 352, 753e819; (d) Fleury-Bregeot, N.; de la
ꢀ
Fuenta, V.; Castillon, S.; Claver, C. ChemCatChem 2010, 2, 1346e1371; (e) Wang,
C.; Villa-Marcos, B.; Xiao, J. Chem. Commun. 2011, 9773e9785; (f) Xie, J.-H.; Zhu,
S.-F.; Zhou, Q.-L. Chem. Rev. 2011, 111, 1713e1760.
3. For selected reviews, see: (a) Noyori, R. Asymmetric Catalysis in Organic Syn-
thesis; Wiley: New York, NY, 1994; (b) Comprehensive Asymmetric Catalysis, Vol.
IeIII; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999.
4. For examples of Ti and Zr catalysis, see: (a) Willoughby, C. A.; Buchwald, S. L. J.
ꢀ
Am. Chem. Soc. 1994, 116, 8952e8965; (b) Campora, J.; Buchwald, S. L.; Gu-
ꢀ
tierrez-Puebla, E.; Monge, A. Organometallics 1995, 14, 2039e2046; (c) Ring-
€
wald, M.; Sturmer, R.; Brintzinger, H. H. J. Am. Chem. Soc. 1999, 121, 1524e1527.
5. For examples of Rh catalysis, see: (a) Burk, M. J.; Feaster, J. E. J. Am. Chem. Soc.
1992, 114, 6266e6267; (b) Lensink, C.; Rijnberg, E.; de Vries, J. G. J. Mol. Catal. A:
Chem. 1997, 116, 199e207; (c) Becalski, A. G.; Cullen, W. R.; Fryzuk, M. D.; James,
B. R.; Kang, G.-J.; Rettig, S. J. Inorg. Chem. 1991, 30, 5002e5008; (d) Buriak, J. M.;
Osborn, J. A. Organometallics 1996, 15, 3161e3169; (e) Spindler, F.; Blaser, H.-U.
Adv. Synth. Catal. 2001, 343, 68e70; (f) Shang, G.; Yang, Q.; Zhang, X. Angew.
Chem., Int. Ed. 2006, 45, 6360e6362.
6. For examples of Ru catalysis, see: (a) Abdur-Rashid, K.; Lough, A. J.; Morris, R. H.
Organometallics 2001, 20, 1047e1049; (b) Cobley, C. J.; Henschke, J. P. Adv. Synth.
Catal. 2003, 345, 195e201; (c) Jackson, M.; Lennon, I. C. Tetrahedron Lett. 2007,
48, 1831e1834; (d) Oppolzer, W.; Wills, M.; Starkemann, C.; Bernardinelli, G.
Tetrahedron Lett. 1990, 31, 4117e4120; (e) Charette, A.; Giroux, A. Tetrahedron
Lett. 1996, 37, 6669e6672; (f) Guan, H.; Iimura, M.; Magee, M. P.; Norton, J. R.;
Zhu, G. J. Am. Chem. Soc. 2005, 127, 7805e7814.
7. For examples of Ir catalysis with P,P-ligands, see: (a) Chan, Y. N. C.; Osborn, J. A.
J. Am. Chem. Soc. 1990, 112, 9400e9401; (b) Spindler, F.; Pugin, B.; Blaser, H.-U.
Angew. Chem., Int. Ed. Engl. 1990, 29, 558e559; (c) Pugin, B.; Landert, H.;
Spindler, F.; Blaser, H.-U. Adv. Synth. Catal. 2002, 344, 17e31; (d) Xiao, D.; Zhang,
X. Angew. Chem., Int. Ed. 2001, 40, 3425e3428; (e) Guiu, E.; Munoz, B.; Castillon,
S.; Claver, C. Adv. Synth. Catal. 2003, 345, 169e171; (f) Dervisi, A.; Carcedo, C.;
Ool, L. Adv. Synth. Catal. 2006, 348, 175e183; (g) Imamoto, T.; Iwadate, N.;
Yoshida, K. Org. Lett. 2006, 8, 2289e2292; (h) Li, W.; Hou, G.; Chang, M.; Zhang,
X. Adv. Synth. Catal. 2009, 351, 3123e3127; (i) Hou, G.; Gosselin, F.; Li, W.;
McWilliams, J. C.; Sun, Y.; Weisel, M.; O’Shea, P. D.; Chen, C.-Y.; Davies, I. W.;
Zhang, X. J. Am. Chem. Soc. 2009, 131, 9882e9883; (j) Jiang, X.-B.; Minnaard, A. J.;
Hessen, B.; Feringa, B. L.; Duchateau, A. L. L.; Andrien, J. G. O.; Boogers, J. A. F.; de
Vries, J. G. Org. Lett. 2003, 5, 1503e1506; (k) Reetz, M. T.; Bondarev, O. Angew.
~
ꢀ
18. For examples of counteranion effect on asymmetric hydrogenation, see: (a)
Smidt, S. P.; Zimmermann, N.; Studer, M.; Pfaltz, A. Chem.dEur. J. 2004, 10,
4685e4693 see also Refs. 8b, 13feh and 14aec.
19. Welch, W. M.; Kraska, A. R.; Sarges, R.; Koe, B. K. J. Med. Chem. 1984, 27,
1508e1515.
ꢁ ꢀ
Chem., Int. Ed. 2007, 46, 4523e4526; (l) Mrsic, N.; Minnaard, A. J.; Feringa, B. L.;
de Vries, J. G. J. Am. Chem. Soc. 2009, 131, 8358e8359; (m) Hou, G.; Tao, R.; Sun,
Y.; Zhang, X.; Gosselin, F. J. Am. Chem. Soc. 2010, 132, 2124e2125; (n) Gao, K.; Yu,
C.-B.; Li, W.; Zhou, Y.-G.; Zhang, X. Chem. Commun. 2011, 7845e7847; (o) Chang,
M.; Li, W.; Zhang, X. Angew. Chem., Int. Ed. 2011, 50, 10679e10681.
20. Addition of 1 equiv CD3OD to solution of 13a and 1.0 mol % 2f in dichloro-
methane in the absence of H2 at room temperature for 0.5 h gave the deu-
terated 13a (approximate 0.5 D at the b-position).
8. For e
ˇ
xamples of Ir catalysis with P,N-ligands, see: (a) Schnider, P.; Koch, G.;
ꢂ
€
21. (a) Aberg, J. B.; Samec, J. S. M.; Bachvall, J. E. Chem. Commun. 2006, 2771e2773;
(b) Blackmond, D. G.; Ropic, M.; Stefinovic, M. Org. Process Res. Dev. 2006, 10,
457e463; (c) Martins, J. E. D.; Clarkson, G. J.; Wills, M. Org. Lett. 2009, 11,
847e850.
ꢀ
€
Pretot, R.; Wang, G.; Bohnen, F. M.; Kruger, C.; Pfaltz, A. Chem.dEur. J. 1997, 3,
887e892; (b) Kainz, S.; Brinkmann, A.; Leitner, W.; Pfaltz, A. J. Am. Chem. Soc.
1999, 121, 6421e6429; (c) Solinas, M.; Pfaltz, A.; Cozzi, P. G.; Leitner, W. J. Am.
Chem. Soc. 2004, 126, 16142e16147; (d) Baeza, A.; Pfaltz, A. Chem.dEur. J. 2010,
16, 4003e4009; (e) Trifonova, A.; Diesen, J. S.; Chapman, C. J.; Andersson, P. G.
Org. Lett. 2004, 6, 3825e3827; (f) Trifonova, A.; Diesen, J. S.; Andersson, P. G.
Chem.dEur. J. 2006, 12, 2318e2328; (g) Cheemala, M. N.; Knochel, P. Org. Lett.
2007, 9, 3089e3092; (h) Moessner, C.; Bolm, C. Angew. Chem., Int. Ed. 2005, 44,
7564e7567; (i) Zhu, S.-F.; Xie, J.-B.; Zhang, Y.-Z.; Li, S.; Zhou, Q.-L. J. Am. Chem.
Soc. 2006, 128, 12886e12891; (j) Han, Z.; Wang, Z.; Zhang, X.; Ding, K. Angew.
Chem., Int. Ed. 2009, 48, 5345e5349.
22. For a comprehensive review, see: Walsh, P. J.; Li, D.; de Parrodi, C. A. Chem. Rev.
2007, 107, 2503e2545.
23. To date, only three examples of transition-metal-catalyzed asymmetric hy-
drogenation under solvent-free conditions were reported, see: (a) Wan, X.; Sun,
Y.; Luo, Y.; Dao, L.; Zhang, Z. J. Org. Chem. 2005, 70, 1070e1072 see also Refs. 6a
and 13d.
24. Sterling, J.; Herzig, Y.; Goren, T.; Finkelstein, N.; Lerner, D.; Goldenberg, W.;
Miskolczi, I.; Molnar, S.; Rantal, F.; Tamas, T.; Toth, G.; Zagyva, A.; Zekany, A.;
Lavian, G.; Gross, A.; Friedman, R.; Razin, M.; Huang, W.; Krais, B.; Chorev, M.;
Youdim, M. B.; Weinstock, M. J. Med. Chem. 2002, 45, 5260e5279.
25. Achiral counteranion-induced reversal of enantioselectivity is rather limited,
for examples, see: (a) Bernardi, A.; Colombo, G.; Scolastico, C. Tetrahedron Lett.
1996, 37, 8921e8924; (b) Carbone, P.; Desimoni, G.; Faita, G.; Filippone, S.;
Righetti, P. Tetrahedron 1998, 54, 6099e6110; (c) Evans, D. A.; Kozlowski, M. C.;
Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem.
Soc. 1999, 121, 669e685; (d) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay,
S. W. J. Am. Chem. Soc. 1999, 121, 686e699; (e) Okamoto, M.; Yamamoto, Y.;
Sakaguchi, S. Chem. Commun. 2009, 7363e7365.
9. For examples of Pd catalysis, see: (a) Abe, H.; Amii, H.; Uneyama, K. Org. Lett.
2001, 3, 313e315; (b) Yang, Q.; Shang, G.; Gao, W.; Deng, J.; Zhang, X. Angew.
Chem., Int. Ed. 2006, 45, 3832e3835; (c) Wang, Y.-Q.; Lu, S.-M.; Zhou, Y.-G. J. Org.
Chem. 2007, 72, 3729e3734; (d) Wang, Y.-Q.; Yu, C.-B.; Wang, D.-W.; Wang, X.-
B.; Zhou, Y.-G. Org. Lett. 2008, 10, 2071e2074; (e) Yu, C.-B.; Wang, D.-W.; Zhou,
Y.-G. J. Org. Chem. 2009, 74, 5633e5635; (f) Chen, M.-W.; Duan, Y.; Chen, Q.-A.;
Wang, D.-S.; Yu, C.-B.; Zhou, Y.-G. Org. Lett. 2010, 12, 5075e5077; (g) Yu, C.-B.;
Gao, K.; Wang, D.-S.; Shi, L.; Zhou, Y.-G. Chem. Commun. 2011, 5052e5054.
10. Fache, F.; Schulz, E.; Tommasino, M. L.; Lemaire, M. Chem. Rev. 2000, 100,
2159e2232.
11. For selected reviews on metal-catalyzed asymmetric transfer hydrogenation,
see: (a) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97e102; (b) Gladiali,
S.; Alberico, E. Chem. Soc. Rev. 2006, 35, 226e236 For pioneering contribution,
26. Haack, K.-J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed.
1997, 36, 285e288.