(2R)-2-Decyl-2,3,4,6,7,8-hexahydroquinolin-5(1H)-one (2w)11.
Chan, Principles and Applications of Asymmetric Synthesis, Wiley-
Interscience, New York, 2001; (d) J. G. de Vries and C. J. Elsevier,
ed., The Handbook of Homogeneous Hydrogeantion, Vol. I–III, Wiley-
VCH, Weinheim, 2007.
3 For recent reviews on asymmetric hydrogenation of heteroaromatic
compounds, see: (a) F. Glorius, Org. Biomol. Chem., 2005, 3, 4171;
(b) Y. G. Zhou, Acc. Chem. Res., 2007, 40, 1357; (c) R. Kuwano,
Heterocycles, 2008, 76, 909.
1
92% ee, [a]2D4 = +112.7 (c 0.06, CH2Cl2). H NMR (400 MHz,
CDCl3) d 4.43 (br, s, 1H), 3.19–3.21 (m, 1H), 2.47–2.51 (dt, 1H,
J = 4.86, 16.08 Hz), 2.26–2.33 (m, 4H), 2.19–2.21 (m, 1H), 1.86–
1.95 (m, 3H), 1.25–1.48 (m, 19H), 0.85–0.89 (m, 3H); 13C NMR
(100.6 MHz, CDCl3) d 195.2, 159.2, 106.0, 52.4, 37.3, 36.6, 32.7,
30.41, 30.39, 30.35, 30.33, 30.1, 27.9, 26.5, 23.5, 22.6, 19.2, 14.9;
HRMS (ESI) calcd. for C19H34NO [M + H]+: 292.2640, found:
292.2646; HPLC (OD-H, elute: hexane/iPrOH = 90/10, detector:
254 nm, flow rate: 1.0 mL min-1), (R) t1 = 8.2 min, (S) t2 = 10.8 min.
4 For asymmetric hydrogenation of quinolines, see: (a) W. B. Wang, S. M.
Lu, P. Y. Yang, X. W. Han and Y. G. Zhou, J. Am. Chem. Soc., 2003,
125, 10536; (b) P. Y. Yang and Y. G. Zhou, Tetrahedron: Asymmetry,
2004, 15, 1145; (c) S. M. Lu, X. W. Han and Y. G. Zhou, Adv. Synth.
Catal., 2004, 346, 909; (d) S. M. Lu, Y. Q. Wang, X. W. Han and Y. G.
Zhou, Angew. Chem., Int. Ed., 2006, 45, 2260; (e) X.-B. Wang and Y.-G.
Zhou, J. Org. Chem., 2008, 73, 5640; (f) D. W. Wang, X. B. Wang, D. S.
Wang, S. M. Lu, Y. G. Zhou and Y. X. Li, J. Org. Chem., 2009, 74,
2780; (g) L. Xu, K. Lam, J. Ji, J. Wu, Q. H. Fan, W. H. Lo and A. S. C.
Chan, Chem. Commun., 2005, 1390; (h) K. Lam, L. Xu, L. Feng, Q.
Fan, F. Lam, W. Lo and A. S. C. Chan, Adv. Synth. Catal., 2005, 347,
1755; (i) L. Qiu, F. Kwong, J. Wu, W. Lam, S. Chan, W. Yu, Y. Li, R.
Guo, Z. Zhou and A. S. C. Chan, J. Am. Chem. Soc., 2006, 128, 5955;
(j) W. J. Tang, S. F. Zhu, L. J. Xu, Q. L. Zhou, Q. H. Fan, H. F. Zhou,
K. Lam and A. S. C. Chan, Chem. Commun., 2007, 613; (k) Z. J. Wang,
G. J. Deng, Y. Li, Y. M. He, W. J. Tang and Q. H. Fan, Org. Lett., 2007,
9, 1243; (l) S. H. Chan, K. H. Lam, Y. M. Li, L. J. Xu, W. J. Tang, F. L.
Lam, W. H. Lo, W. Y. Yu, Q. H. Fan and A. S. C. Chan, Tetrahedron:
Asymmetry, 2007, 18, 2625; (m) H. F. Zhou, Z. W. Li, Z. J. Wang, T. L.
Wang, L. J. Xu, Y. M. He, Q.H. Fan, J. Pan, L. Q. Gu and A. S. C. Chan,
Angew. Chem., Int. Ed., 2008, 47, 8464; (n) Z. W. Li, T. L. Wang, Y. M.
He, Z. J. Wang, Q. H. Fan, J. Pan and L. J. Xu, Org. Lett., 2008, 10,
5265; (o) Z. J. Wang, H. F. Zhou, T. L. Wang, Y. M. He and Q. H. Fan,
Green Chem., 2009, 11, 767; (p) M. Reetz and X. Li, Chem. Commun.,
2006, 2159; (q) C. Deport, M. Buchotte, K. Abecassis, H. Tadaoka, T.
Ayael, T. Ohshima, J. P. Geneˆt, K. Mashima and V. Ratovelomanana-
Vidal, Synlett, 2007, 2743; (r) N. Mrsic, L. Lefort, J. A. F. Boogers,
A. J. Minnaard, B. L. Feringa and J. G. de Vries, Adv. Synth. Catal.,
2008, 350, 1081; (s) S. M. Lu and C. Bolm, Adv. Synth. Catal., 2008,
(2S)-2-Phenyl-2,3,4,6,7,8-hexahydroquinolin-5(1H)-one (2x).
1
89% ee, [a]2D4 = +199.1 (c 0.05, CH2Cl2). H NMR (400 MHz,
CDCl3) d 7.25–7.38 (m, 5H), 4.96 (br, s, 1H), 4.38–4.40 (m, 1H),
2.32–2.42 (m, 6H), 1.95–2.06 (m, 3H), 1.79–1.83 (m, 1H); 13C
NMR (100.6 MHz, CDCl3) d 195.3, 159.5, 143.5, 129.5, 128.6,
127.1, 105.9, 56.7, 37.3, 30.7, 30.1, 22.6, 18.8; HRMS (ESI)
calcd. for C15H18NO [M + H]+: 228.1388, found: 228.1385; HPLC
(AS-H, elute: hexane/iPrOH = 80/20, detector: 254 nm, flow
rate: 1.0 mL min-1), (S) t1 = 29.4 min, (R) t2 = 38.6 min.
(2S)-2-Benzyl-2,3,4,6,7,8-hexahydroquinolin-5(1H)-one (2y).
1
97% ee, [a]2D4 = +107.8 (c 0.05, CH2Cl2). H NMR (400 MHz,
CDCl3) d 7.33–7.37 (m, 2H), 7.26–7.29 (m, 1H), 7.19–7.21 (m,
2H), 4.51 (br, s, 1H), 3.49–3.51 (m, 1H), 2.84–2.89 (dd, 1H, J =
5.6, 13.46 Hz), 2.67–2.72 (dd, 1H, J = 8.82, 13.44 Hz), 2.51–2.58
(dt, 1H, J = 5.36, 16.16 Hz), 2.21–2.35 (m, 5H), 1.90–1.98 (m, 3H),
1.55–1.60 (m, 1H); 13C NMR (100.6 MHz, CDCl3) d 195.3, 159.0,
138.4, 129.9, 129.6, 127.6, 106.0, 53.35, 42.8, 37.3, 30.2, 27.9,
22.5, 18.9; HRMS (ESI) calcd. for C16H20NO [M + H]+: 242.1545,
found: 242.1550; HPLC (OD-H, elute: hexane/iPrOH = 90/10,
detector: 254 nm, flow rate: 1.0 mL min-1), (R) t1 = 22.2 min, (S)
t2 = 24.9 min.
350, 1101; (t) M. Egenstein, A. Thomas, J. Theuerkauf, G. Francio`
and W. Leitner, Adv. Synth. Catal., 2009, 351, 725; (u) H. Tadaoka,
D. Cartigny, T. Nagano, T. Gosavi, T. Ayad, J. P. Geneˆt, T. Ohshima,
V. Ratovelomanana-Vidal and K. Mashima, Chem.–Eur. J., 2009, 15,
9990; (v) D. Wang, J. Zhou, D. Wang, Y. Guo and Y. Zhou, Tetrahedron
Lett., 2010, 51, 525.
5 For asymmetric hydrogenation of quinoxalines, see: (a) S. Murata,
T. Sugimoto and S. Matsuura, Heterocycles, 1987, 26, 763; (b) C.
Bianchini, P. Barbaro, G. Scapacci, E. Farnetti and M. Graziani,
Organometallics, 1998, 17, 3308; (c) C. Bianchini, P. Barbaro and G.
Scapacci, J. Organomet. Chem., 2001, 621, 26; (d) C. J. Cobley and J. P.
Henschke, Adv. Synth. Catal., 2003, 345, 195; (e) J. P. Henschke, M. J.
Burk, C. G. Malan, D. Herzberg, J. A. Peterson, A. J. Wildsmith, C. J.
Cobley and G. Casy, Adv. Synth. Catal., 2003, 345, 300; (f) W. J. Tang,
L. J. Xu, Q. H. Fan, J. Wang, B. M. Fan, K. H. Lam and A. S. C. Chan,
Angew. Chem., Int. Ed., 2009, 48, 9135; (g) N. Mrsˇic´, T. Jerphagnon,
A. J. Minnaard, B. L. Feringa and J. G. de Vries, Adv. Synth. Catal.,
2009, 351, 2549.
6 For asymmetric hydrogenation of furans, see: (a) T. Ohta, T. Miyake, N.
Seido, H. Kumobayashi and H. Takaya, J. Org. Chem., 1995, 60, 357;
(b) S. Kaiser, S. P. Smidt and A. Pfaltz, Angew. Chem., Int. Ed., 2006,
45, 5194; (c) P. Feiertag, M. Albert, U. Nettekoven and F. Spindler,
Org. Lett., 2006, 8, 4133.
(2R)-2-(2-Phenylethyl)-2,3,4,6,7,8-hexahydroquinolin-5(1H)-
1
one (2z)11. 90% ee, [a]D24 = +209.5 (c 0.1, CH2Cl2). H NMR
(400 MHz, CDCl3) d 7.18–7.31 (m, 5H), 4.40 (br, s, 1H), 3.26–3.28
(m, 1H), 2.66–2.79 (m, 1H), 2.44–2.50 (dt, 1H, J = 5.36, 16.15
Hz), 2.29–2.32 (m, 2H), 2.18–2.26 (m, 3H), 1.79–1.92 (m, 5H),
1.50–1.54 (m, 1H); 13C NMR (100.6 MHz, CDCl3) d 195.2, 159.0,
142.1, 129.4, 129.1, 127.0, 105.9, 52.0, 37.9, 37.3, 33.0, 30.2, 27.7,
22.5, 18.8; HRMS (ESI) calcd. for C17H22NO [M + H]+: 256.1701,
found: 256.1708; HPLC (OD-H, elute: hexane/iPrOH = 80/20,
detector: 254 nm, flow rate: 1.0 mL min-1), (R) t1 = 10.1 min, (S)
t2 = 12.1 min.
Acknowledgements
7 For asymmetric hydrogenation of pyrroles, see: R. Kuwano, M.
Kashiwabara, M. Ohsumi and H. Kusano, J. Am. Chem. Soc., 2008,
130, 808.
The authors would like to thank NSFC under grant No. 20873179
and MOST under grant No 2007CB935902 for financial supports.
8 For asymmetric hydrogenation of pyridines, see: (a) S. A. Raynor,
J. M. Thomas, R. Raja, B. F. G. Johnson, R. G. Belle and M. D.
Mantle, Chem. Commun., 2000, 1925; (b) M. Studer, C. Wedemeyer-
Exl, F. Spindler and H.-U. Blaser, Monatsh. Chem., 2000, 131, 1335;
(c) H.-U. Blaser, H. Ho¨x00A8;ning, M. Studer and C. Wedemeyer-
Exl, J. Mol. Catal. A: Chem., 1999, 139, 253; (d) C. Y. Legault
and A. B. Charette, J. Am. Chem. Soc., 2005, 127, 8966; (e) C. Y.
Legault, A. B. Charette and P. G. Cozzi, Heterocycles, 2008, 76, 1271;
(f) X. B. Wang, W. Zeng and Y. G. Zhou, Tetrahedron Lett., 2008, 49,
4922.
Notes and references
1 For comprehensive reviews, see: (a) D. H. R. Barton, K. Nakanishi and
O. Meth-Cohn, Comprehensive Nature Products Chemistry, Elsevier,
Oxford, UK, 1999, Vol 1–9; (b) A. R. Katritzky, S. Rachwal and B.
Rachwal, Tetrahedron, 1996, 52, 15031.
2 (a) H.-U. Blaser, C. Malan, B. Pugin, F. Splindler, H. Steiner and
M. Studer, Adv. Synth. Catal., 2003, 345, 103; (b) W. Tang and X.
Zhang, Chem. Rev., 2003, 103, 3029; (c) G. Lin, Y. Li and A. S. C.
9 For asymmetric hydrogenation of indoles, see: (a) R. Kuwano, K. Sato,
T. Kurokawa, D. Karube and Y. Ito, J. Am. Chem. Soc., 2000, 122,
3470 | Org. Biomol. Chem., 2010, 8, 3464–3471
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