M. Perez, Z. Wu, M. Scalone, T. Ayad, V. Ratovelomanana-Vidal
FULL PAPER
T. Ikariya, A. J. Blacker, Acc. Chem. Res. 2007, 40, 1300; j)
A. J. Blacker, in: Handbook of Homogeneous Hydrogenation
(Eds.: J. G. de Vries, C. J. Elsevier), Wiley-VCH, Weinheim,
Germany, 2007, pp 1215–1244; k) C. Wang, X. Wu, J. Xiao,
Chem. Asian J. 2008, 3, 1750; l) T. Ikariya, Bull. Chem. Soc.
Jpn. 2011, 84, 1; m) A. Bartoszewicz, N. Ahlsten, B. Martín-
Matute, Chem. Eur. J. 2013, 19, 7274.
R. Noyori, J. Am. Chem. Soc. 1996, 118, 4916; b) E. Vedejs, P.
Trapencieris, E. Suna, J. Org. Chem. 1999, 64, 6724; c) J. Wu,
F. Wang, Y. Ma, X. Cui, L. Cun, J. Zhu, J. Deng, B. Yu, Chem.
Commun. 2006, 1766; d) L. Evanno, J. Ormala, P. M. Pihko,
ˇ
Chem. Eur. J. 2009, 15, 12963; e) J. Prˇech, J. Václavík, P. Sot,
J. Pechácˇek, B. Vilhanová, J. Janusˇcˇák, K. Syslová, R. Pazout,
ˇ
J. Maixner, J. Zápal, M. Kuzma, P. Kacˇer, Catal. Commun.
2013, 36, 67; f) Z. Wu, M. Perez, M. Scalone, T. Ayad, V. Rato-
velomanana-Vidal, Angew. Chem. Int. Ed. 2013, 52, 4925; An-
gew. Chem. 2013, 125, 5025; g) T. Quinto, F. Schwizer, J. M.
Zimbron, A. Morina, V. Kçhler, T. R. Ward, ChemCatChem
2014, 6, 1010.
[17] For representative examples of catalytic asymmetric hydrogen-
ation of 1-alkyl-3,4-DHIQs, see: a) C. A. Willoughby, S. L.
Buchwald, J. Am. Chem. Soc. 1994, 116, 8952; b) T. Morimoto,
N. Nakajima, K. Achiwa, Tetrahedron: Asymmetry 1995, 6, 75;
c) T. Morimoto, K. Achiwa, Tetrahedron: Asymmetry 1995, 6,
2661; d) T. Morimoto, N. Suzuki, K. Achiwa, Tetrahedron:
Asymmetry 1998, 9, 183; e) G. Zhu, X. Zhang, Tetrahedron:
Asymmetry 1998, 9, 2415; f) J. Cobley, J. P. Henschke, Adv.
Synth. Catal. 2003, 345, 195; g) E. Guiu, C. Claver, J. Benet-
Buchholz, S. Castillon, Tetrahedron: Asymmetry 2004, 15,
3365; h) S. M. Lu, Y. Q. Wang, X. W. Han, L. X. Wang, Q. L.
Zhou, Angew. Chem. Int. Ed. 2006, 45, 2260; Angew. Chem.
2006, 118, 2318; i) M. Jackson, I. C. Lennon, Tetrahedron Lett.
2007, 48, 1831; j) C. Li, J. Xiao, J. Am. Chem. Soc. 2008, 130,
13208; k) P. C. Yan, J. H. Xie, G. H. Hou, L. X. Wang, Q. L.
Zhou, Adv. Synth. Catal. 2009, 351, 3243; l) J. H. Xie, P. C.
Yan, Q. Q. Zhang, K. X. Yuan, Q. L. Zhou, ACS Catal. 2012,
2, 561; m) Z. Y. Ding, T. Wang, Y. M. He, F. Chen, H. F. Zhou,
Q. H. Fan, Q. Guo, A. S. C. Chan, Adv. Synth. Catal. 2013,
355, 3727; n) G. K. M. Verzijl, A. H. M. de Vries, J. G. de Vries,
P. Kapitan, T. Dax, M. Helms, Z. Nazir, W. Skranc, C. Im-
boden, J. Stichler, R. A. Ward, S. Abele, L. Lefort, Org. Process
Res. Dev. 2013, 17, 1531.
[18] For representative examples of catalytic asymmetric transfer
hydrogenation of 1-alkyl-3,4-DHIQs, see: a) J. Mao, D. C.
Baker, Org. Lett. 1999, 1, 841; b) L. F. Tietze, Y. Zhou, E.
Töpken, Eur. J. Org. Chem. 2000, 2247; c) G. D. Williams,
R. A. Pike, C. E. Wade, M. Wills, Org. Lett. 2003, 5, 4227; d)
L. F. Tietze, N. Rackelmann, G. Sekar, Angew. Chem. Int. Ed.
2003, 42, 4254; Angew. Chem. 2003, 115, 4386; e) L. F. Tietze,
N. Rackelmann, I. Muller, Chem. Eur. J. 2004, 10, 2722; J.
Szawkalo, Z. Czarnocki, Monatsh. Chem. 2005, 136, 1619; f)
D. Mujahidin, S. Doye, Eur. J. Org. Chem. 2005, 2689; g) P.
Roszkowski, J. K. Maurin, Z. Czarnocki, Tetrahedron: Asym-
metry 2006, 17, 1415; h) J. Canivet, G. Süss-Fink, Green Chem.
2007, 9, 391; i) L. Li, J. Wu, F. Wang, J. Liao, H. Zhang, C.
Lian, J. Zhu, J. Deng, Green Chem. 2007, 9, 23; j) F. Werner,
N. Blank, T. Opatz, Eur. J. Org. Chem. 2007, 3911; k) S. J. Czar-
nocki, K. Wojtasiewicz, A. P. Joz´wiak, J. K. Maurin, Z. Czar-
nocki, J. Drabowicz, Tetrahedron 2008, 64, 3176; l) D. S. Ma-
tharu, J. E. D. Martins, M. Wills, Chem. Asian J. 2008, 3, 1374;
m) J. E. D. Martins, G. J. Clarkson, M. Wills, Org. Lett. 2009,
11, 847; n) J. E. D. Martins, M. A. C. Redondo, M. Wills, Tet-
rahedron: Asymmetry 2010, 21, 2258.
[21]
a) R. Touati, V. Ratovelomanana-Vidal, B. Ben Hassine, J. P.
Genet, Tetrahedron: Asymmetry 2006, 17, 3400; b) C. Mordant,
S. Reymond, H. Tone, D. Lavergne, R. Touati, B. Ben Hassine,
V. Ratovelomanana-Vidal, J. P. Genet, Tetrahedron 2007, 63,
6115; c) C. Pautigny, S. Jeulin, T. Ayad, Z. G. Zhang, J.-P.
Genet, V. Ratovelomanana-Vidal, Adv. Synth. Catal. 2008, 350,
2525; d) H. Tone, M. Buchotte, C. Mordant, E. Guittet, T.
Ayad, V. Ratovelomanana-Vidal, Org. Lett. 2009, 11, 1995; e)
H. Tadaoka, D. Cartigny, T. Nagano, T. Gosavi, T. Ayad, J.-P.
Genet, T. Ohshima, V. Ratovelomanana-Vidal, K. Mashima,
Chem. Eur. J. 2009, 15, 9990; f) C. Pautigny, C. Debouit, P.
Vayron, T. Ayad, V. Ratovelomanana-Vidal, Tetrahedron:
Asymmetry 2010, 21, 1382; g) D. Cartigny, T. Nagano, T. Ayad,
J.-P. Genet, T. Ohshima, K. Mashima, V. Ratovelomanana-Vi-
dal, Adv. Synth. Catal. 2010, 352, 1886; h) Z. Wu, T. Ayad, V.
Ratovelomanana-Vidal, Org. Lett. 2011, 13, 3782; i) S. Prevost,
T. Ayad, P. Phansavath, V. Ratovelomanana-Vidal, Adv. Synth.
Catal. 2011, 353, 3213; j) D. Cartigny, F. Berhal, T. Nagano, P.
Phansavath, T. Ayad, J.-P. Genet, T. Ohshima, K. Mashima,
V. Ratovelomanana-Vidal, J. Org. Chem. 2012, 77, 4544; k) S.
Gauthier, L. Larquetoux, M. Nicolas, T. Ayad, P. Maillos, V.
Ratovelomanana-Vidal, Synlett 2014, 25, 1606; l) P.-G. Echev-
erria, S. Prevost, J. Cornil, J. C. Ferard, S. Reymond, A. Guéri-
not, J. Cossy, V. Ratovelomanana-Vidal, P. Phansavath, Org.
Lett. 2014, 16, 2390; m) P. G. Echeverria, C. Férard, P. Phansa-
vath, V. Ratovelomanana-Vidal, Catal. Commun. 2015, 62, 95.
[22]
[23]
M. Movassaghi, D. Hill, Org. Lett. 2008, 10, 3485.
S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya, R. Noyori, J.
Am. Chem. Soc. 1995, 117, 7562.
[24] a) K.-J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya, R. Noyori,
Angew. Chem. Int. Ed. Engl. 1997, 36, 285; Angew. Chem. 1997,
109, 297; b) D. A. Alonso, P. Brandt, S. J. M. Nordin, P. G.
Andersson, J. Am. Chem. Soc. 1999, 121, 9580; c) M. Yamak-
awa, H. Ito, R. Noyori, J. Am. Chem. Soc. 2000, 122, 1466;
d) G. I. Petra, J. N. H. Reek, J.-W. Handgraaf, E. V. Meijer, P.
Dierkes, P. C. J. Kamer, J. Brussee, H. E. Schoemaker,
P. W. N. M. van Leeuwen, Chem. Eur. J. 2000, 6, 2818; e) R.
Noyori, M. Yamakawa, S. Hashiguchi, J. Org. Chem. 2001, 66,
7931.
[19] a) M. Chang, W. Li, X. Zhang, Angew. Chem. Int. Ed. 2011,
50, 10679; Angew. Chem. 2011, 123, 10867; b) S. Duprat
de Paule, N. Champion, V. Ratovelomanana-Vidal, J. P. Genêt,
P. Dellis, French Patent 2830254, 2001, WO Patent
2003029259, 2003; c) F. Berhal, Z. Wu, Z. G. Zhang, T. Ayad,
V. Ratovelomanana-Vidal, Org. Lett. 2012, 14, 3308; d) M.
[25] a) J. B. Åberg, J. S. M. Samec, J. E. Bäckvall, Chem. Commun.
2006, 2771; b) D. G. Blackmond, M. Ropic, M. Stefinovic, Org.
Process Res. Dev. 2006, 10, 457; c) J. E. D. Martins, G. J.
Clarkson, M. Wills, Org. Lett. 2009, 11, 847; d) R. Soni, F. K.
Cheung, G. C. Clarkson, J. E. D. Martins, M. A. Grahamb, M.
Wills, Org. Biomol. Chem. 2011, 9, 3290; e) J. Václavík, P.
Ruzicˇ, A. Pecˇavar, D. Prudicˇ, D. Kralj, C. Scriban, A. Zanotti-
ˇ
ˇ
Kacˇer, M. Kuzma, L. Cerveny, Molecules 2011, 16, 5460; f) J.
Gerosa, Org. Process Res. Dev. 2012, 16, 1293; e) A. Iimuro,
K. Yamaji, S. Kandula, T. Nagano, Y. Kita, K. Mashima, An-
gew. Chem. Int. Ed. 2013, 52, 2046; Angew. Chem. 2013, 125,
2100.
Václavík, M. Kuzma, J. Prˇech, P. Kacˇer, Organometallics 2011,
ˇ
30, 4822; g) P. Sot, M. Kuzma, J. Václavík, J. Pechácˇek, J.
Prˇech, J. Januscˇk, P. Kacˇer, Organometallics 2012, 31, 6496.
Received: July 20, 2015
Published Online: September 3, 2015
[20] For catalytic asymmetric transfer hydrogenation of 1-aryl-3,4-
DHIQs, see: a) N. Uematsu, A. Fujii, S. Hashiguchi, T. Ikariya,
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