COMMUNICATIONS
Jianheng Ye et al.
Acids, 2nd edn., (Eds.: E. Juaristi, V. A. Soloshonok),
John Wiley & Sons, Inc., 2005, pp 19–75.
[2] S. Kang, H.-K. Lee, J. Org. Chem. 2010, 75, 237–240.
[3] S. J. Haycock-Lewandowski, A. Wilder, J. hman, Org.
Process Res. Dev. 2008, 12, 1094–1103.
[7] Recent reviews of Lewis bases-catalyzed hydrogena-
ˇ
´
tion, see: a) P. Kocovsky, A. V. Malkov, in: Enantiose-
lective Organocatalysis, Wiley-VCH, 2007, pp 255–286;
b) S. E. Denmark, G. L. Beutner, Angew. Chem. 2008,
120, 1584–1663; Angew. Chem. Int. Ed. 2008, 47, 1560–
1638; c) Z. Zhang, Synlett 2008, 1915–1916; d) S. Guiz-
zetti, M. Benaglia, Eur. J. Org. Chem. 2010, 5529–5541;
e) S. Jones, C. J. A. Warner, Org. Biomol. Chem. 2012,
10, 2189–2200; f) Y. B. Liu, H. F. Du, Acta Chim. Sinica
2014, 72, 771–777.
[4] For reviews, see: a) J.-A. Ma, Angew. Chem. 2003, 115,
4426–4435; Angew. Chem. Int. Ed. 2003, 42, 4290–4299;
b) J. H. Cohen, M. E. Bos, S. Cesco-Cancian, B. D.
Harris, J. T. Hortenstine, M. Justus, C. A. Maryanoff, J.
Mills, S. Muller, A. Roessler, L. Scott, K. L. Sorgi, F. J.
Villani, R. R. H. Webster, C. Weh, Org. Process Res.
Dev. 2003, 7, 866–872; c) N. Ikemoto, D. M. Tellers,
S. D. Dreher, J. Liu, A. Huang, N. R. Rivera, E. Njolito,
Y. Hsiao, J. C. McWilliams, J. M. Williams, J. D. Arm-
strong, Y. Sun, D. J. Mathre, E. J. J. Grabowski, R. D.
Tillyer, J. Am. Chem. Soc. 2004, 126, 3048–3049; d) H.
Shimizu, I. Nagasaki, K. Matsumura, N. Sayo, T. Saito,
Acc. Chem. Res. 2007, 40, 1385–1393; e) D. Steinhuebel,
Y. Sun, K. Matsumura, N. Sayo, T. Saito, J. Am. Chem.
Soc. 2009, 131, 11316–11317; f) L. Kiss, M. Cherepano-
va, F. Fülçp, Tetrahedron 2015, 71, 2049–2069.
[5] Recent reviews of transition metal-catalyzed hydroge-
nation, see: a) W. Tang, X. Zhang, Chem. Rev. 2003,
103, 3029–3070; b) E. Juaristi, V. M. GutiØrrez-García,
H. López-Ruiz, in: Enantioselective Synthesis of b-
Amino Acids, John Wiley & Sons, Inc., 2005, pp 159–
179; c) B. Weiner, W. Szymanski, D. B. Janssen, A. J.
Minnaard, B. L. Feringa, Chem. Soc. Rev. 2010, 39,
1656–1691; d) J.-H. Xie, S.-F. Zhu, Q.-L. Zhou, Chem.
Rev. 2011, 111, 1713–1760; e) J.-H. Xie, S.-F. Zhu, Q.-L.
Zhou, Chem. Soc. Rev. 2012, 41, 4126–4139.
[6] Selected examples of transition metal-catalyzed hydro-
genation, see: a) M. Yasutake, I. D. Gridnev, N. Higa-
shi, T. Imamoto, Org. Lett. 2001, 3, 1701–1704; b) Y.-G.
Zhou, W. Tang, W.-B. Wang, W. Li, X. Zhang, J. Am.
Chem. Soc. 2002, 124, 4952–4953; c) D. PeÇa, A. J. Min-
naard, J. G. de Vries, B. L. Feringa, J. Am. Chem. Soc.
2002, 124, 14552–14553; d) J. You, H.-J. Drexler, S.
Zhang, C. Fischer, D. Heller, Angew. Chem. 2003, 115,
942–945; Angew. Chem. Int. Ed. 2003, 42, 913–916;
e) Y. Hsiao, N. R. Rivera, T. Rosner, S. W. Krska, E.
Njolito, F. Wang, Y. Sun, J. D. Armstrong, E. J. J. Gra-
bowski, R. D. Tillyer, F. Spindler, C. Malan, J. Am.
Chem. Soc. 2004, 126, 9918–9919; f) H.-P. Wu, G. Hoge,
Org. Lett. 2004, 6, 3645–3647; g) K. B. Hansen, T.
Rosner, M. Kubryk, P. G. Dormer, J. D. Armstrong,
Org. Lett. 2005, 7, 4935–4938; h) Q. Dai, W. Yang, X.
Zhang, Org. Lett. 2005, 7, 5343–5345; i) X.-B. Wang,
D.-W. Wang, S.-M. Lu, C.-B. Yu, Y.-G. Zhou, Tetrahe-
dron: Asymmetry 2009, 20, 1040–1045; j) G. F. Bussch-
er, L. Lefort, J. G. O. Cremers, M. Mottinelli, R. W.
Wiertz, B. d. Lange, Y. Okamura, Y. Yusa, K. Matsu-
mura, H. Shimizu, J. G. de Vries, A. H. M. de Vries,
Tetrahedron: Asymmetry 2010, 21, 1709–1714; k) G.
Hou, W. Li, M. Ma, X. Zhang, X. Zhang, J. Am. Chem.
[8] Selected examples of Lewis bases-catalyzed asymmetric
reduction of b-enamino esters, see: a) H. Zheng, J.
Deng, W. Lin, X. Zhang, Tetrahedron Lett. 2007, 48,
7934–7937; b) H.-J. Zheng, W.-B. Chen, Z.-J. Wu, J.-G.
Deng, W.-Q. Lin, W.-C. Yuan, X.-M. Zhang, Chem.
Eur. J. 2008, 14, 9864–9867; c) A. V. Malkov, S. Ston-
cius, K. Vrankova, M. Arndt, P. Kocovsky, Chem. Eur.
J. 2008, 14, 8082–8085; d) Z.-Y. Xue, Y. Jiang, W.-C.
Yuan, X.-M. Zhang, Eur. J. Org. Chem. 2010, 616–619;
e) S. Guizzetti, M. Benaglia, M. Bonsignore, L. Rai-
mondi, Org. Biomol. Chem. 2011, 9, 739–743; f) X.
Chen, Y. Zheng, C. Shu, W. Yuan, B. Liu, X. Zhang, J.
Org. Chem. 2011, 76, 9109–9115; g) X. Wu, Y. Li, C.
Wang, L. Zhou, X. Lu, J. Sun, Chem. Eur. J. 2011, 17,
2846–2848; h) Y. Jiang, X. Chen, Y. Zheng, Z. Xue, C.
Shu, W. Yuan, X. Zhang, Angew. Chem. 2011, 123,
7442–7445; Angew. Chem. Int. Ed. 2011, 50, 7304–7307;
i) S. Guizzetti, M. Benaglia, M. Bonsignore, L. Raimon-
di, Org. Biomol. Chem. 2011, 9, 739–743; j) S. Jones, X.
Li, Tetrahedron 2012, 68, 5522–5532; k) Z.-Y. Xue, L.-
X. Liu, Y. Jiang, W.-C. Yuan, X.-M. Zhang, Eur. J. Org.
Chem. 2012, 251–255; l) X. Chen, X.-Y. Hu, C. Shu, Y.-
H. Zhang, Y.-S. Zheng, Y. Jiang, W.-C. Yuan, B. Liu,
X.-M. Zhang, Org. Biomol. Chem. 2013, 11, 3089–3093.
[9] a) D. Wang, D. Astruc, Chem. Rev. 2015, 115, 6621–
6686;b) Y. J. Wang, Z. F. Zhang, W. B. Zhang, Chin. J.
Org. Chem. 2015, 35, 528–538.
[10] O. Onomura, Y. Kouchi, F. Iwasaki, Y. Matsumura, Tet-
rahedron Lett. 2006, 47, 3751–3754.
[11] The role of water is to react with HSiCl3, and release
a proton to facilitate the tautomerization of enamine to
imine, see: a) X. Wu, Y. Li, C. Wang, L. Zhou, X. Lu, J.
Sun, Chem. Eur. J. 2011, 17, 2846–2848; b) Y. C. Xiao,
C. Wang, Y. Yao, J. Sun, Y. C. Chen, Angew. Chem.
2011, 123, 10849–10852; Angew. Chem. Int. Ed. 2011,
50, 10661–10664; c) X. W. Liu, Y. Yan, Y. Q. Wang, C.
Wang, J. Sun, Chem. Eur. J. 2012, 18, 9204–9207; d) L.
Chen, C. Wang, L. Zhou, J. Sun, Adv. Synth. Catal.
2014, 356, 2224–2230.
[12] P. You, J. Qiu, E. Su, D. Wei, Eur. J. Org. Chem. 2013,
2013, 557–565.
[13] a) K. B. Hansen, Y. Hsiao, F. Xu, N. Rivera, A. Clau-
sen, M. Kubryk, S. Krska, T. Rosner, B. Simmons, J.
Balsells, N. Ikemoto, Y. Sun, F. Spindler, C. Malan,
E. J. J. Grabowski, J. D. Armstrong, J. Am. Chem. Soc.
2009, 131, 8798–8804; b) A. A. Desai, Angew. Chem.
2011, 123, 2018–2020; Angew. Chem. Int. Ed. 2011, 50,
1974–1976; c) S. G. Davies, A. M. Fletcher, L. Lv, P. M.
Roberts, J. E. Thomson, Tetrahedron Lett. 2012, 53,
3052–3055; d) K. Lin, Z. Cai, W. Zhou, Synth.
Commun. 2013, 43, 3281–3286; e) C. S. Subbaiah, W.
Haq, Tetrahedron: Asymmetry 2014, 25, 1026–1030;
ˇ ´
Soc. 2010, 132, 12844–12846; l) N. Mrsic, L. Panella,
A. J. Minnaard, B. L. Feringa, J. G. de Vries, Tetrahe-
dron: Asymmetry 2011, 22, 36–39; m) M. AmØzquita-
Valencia, A. Cabrera, J. Organomet. Chem. 2014, 768,
145–150; n) P. Yang, H. Xu, J. Zhou, Angew. Chem.
2014, 126, 5201–5205; Angew. Chem. Int. Ed. 2014, 53,
12210–12213.
1046
ꢁ 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2016, 358, 1042 – 1047