and K. Maruoka, Tetrahedron, 2008, 64, 1197–1203; (g) B. T. Hahn,
R. Fröhlich, K. Harms and F. Glorius, Angew. Chem., Int. Ed., 2008, 47,
9985–9988; (h) M. Pouliquen, J. Blanchet, M.-C. Lasne and J. Rouden,
Org. Lett., 2008, 10, 1029–1032; (i) I. Ibrahem and A. Córdova, Chem.
Commun., 2006, 1760–1762; ( j) H. Zhang, Y. M. Chuan, Z. Y. Li and
Y. G. Peng, Adv. Synth. Catal., 2009, 351, 2288–2294; (k) J. Pietruszka
and R. C. Simon, ChemCatChem, 2010, 2, 505–508; (l) R. Martín-Rapún,
X. Y. Fan, S. Sayalero, M. Bahramnejad, F. Cuevas and M. A. Pericàs,
Chem.–Eur. J., 2011, 17, 8780–8783; (m) J. Franzén, M. Marigo,
D. Fielenbach, T. C. Wabnitz, A. Kjærsgaard and K. A. Jørgensen, J. Am.
Chem. Soc., 2005, 127, 18296–18304; (n) T. Kano, Y. Hato and
K. Maruoka, Tetrahedron Lett., 2006, 47, 8467–8469; (o) P. Dziedzic and
A. Córdova, Tetrahedron: Asymmetry, 2007, 18, 1033–1037.
CDCl3) δ 9.70 (d, J = 1.1 Hz, 1H), 8.17–8.20 (d, J = 7.9 Hz,
2H), 7.45–7.48 (m, 2H), 5.78–5.80 (d, J = 6, Hz, 1H), 5.17
(s, 1H), 2.73 (s, 1H), 2.00–2.03 (m, 1H), 1.41 (s, 9H), 1.09–1.14
(m, 6H). 13C NMR (75 MHz, CDCl3) δ 205.39, 155.05, 148.90,
147.20, 127.46, 123.88, 80.32, 62.10, 52.48, 28.53, 28.27,
21.21, 19.64 ppm. IR (neat): 3335, 3114, 3080, 2970, 2934,
2876, 2740, 1717, 1605, 1523, 1349, 1252, 1167, 1108, 1046,
961, 858, 782, 753, 633 cm−1. HRMS (ESI): calcd For
C17H24N2O5 [M + Na]+ 359.1583; found 359.1593.
Acknowledgements
4 (a) D. Enders and M. Vrettou, Synthesis, 2006, 13, 2155–2158;
(b) D. Enders, C. Grondal and M. Vrettou, Synthesis, 2006, 21, 3597–
3604; (c) J. W. Yang, M. Stadler and B. List, Nat. Protoc., 2007, 2, 1937–
1942; (d) J. W. Yang, M. Stadler and B. List, Angew. Chem., Int. Ed.,
2007, 46, 609–611; (e) J. W. Yang, C. Chandler, M. Stadler, D. Kampen
and B. List, Nature, 2008, 452, 453–455; (f) J. Vesely, R. Rios, I. Ibrahem
and A. Córdova, Tetrahedron Lett., 2007, 48, 421–425; (g) P. Dziedzic,
J. Vesely and A. Córdova, Tetrahedron Lett., 2008, 49, 6631–6634;
(h) N. Utsumi, S. Kitagaki and C. F. Barbas III, Org. Lett., 2008, 10,
3405–3408; (i) N. S. Chowdari, M. Ahmad, K. Albertshofer, F. Tanaka
and C. F. Barbas III, Org. Lett., 2006, 8, 2839–2842; ( j) B. List, J. Am.
Chem. Soc., 2000, 122, 9336–9337; (k) W. Notz, S. Watanabe,
N. S. Chowdari, G. Zhong, J. M. Betancort, F. Tanaka and C. F. Barbas III,
Adv. Synth. Catal., 2004, 346, 1131–1140; (l) B. List, P. Pojarliev,
W. T. Biller and H. J. Martin, J. Am. Chem. Soc., 2002, 124, 827–833;
(m) D. Enders, C. Grondal, M. Vrettou and G. Raabe, Angew. Chem., Int.
Ed., 2005, 44, 4079–4083; (n) A. Córdova, Chem.–Eur. J., 2004, 10,
1987–1997; (o) I. Ibrahem, W. Zou, M. Engqvist, Y. Xu and A. Córdova,
Chem.–Eur. J., 2005, 11, 7024–7029; (p) A. Córdova, Synlett, 2003, 11,
1651–1654; (q) W.-W. Liao, I. Ibrahem and A. Córdova, Chem. Commun.,
2006, 674–676; (r) Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima,
M. Shoji and K. Sakai, Angew. Chem., Int. Ed., 2003, 42, 3677–3680;
(s) Y. Hayashi, T. Urushima, S. Aratake, T. Okano and K. Obi, Org. Lett.,
2008, 10, 21–24; (t) S. Fustero, D. Jiménez, J. F. Sanz-Cervera,
M. Sánchez-Roselló, E. Esteban and A. Simón-Fuentes, Org. Lett., 2005,
7, 3433–3436; (u) I. Ibrahem and A. Córdova, Tetrahedron Lett., 2005, 46,
2839–2843; (v) Y. Hayashi, T. Urushima, M. Shoji, T. Uchimaru and
I. Shiina, Adv. Synth. Catal., 2005, 347, 1595–1604; (w) M. L. Kantam,
C. V. Rajasekhar, G. Gopikrishna, K. R. Reddy and B. M. Choudary,
Tetrahedron Lett., 2006, 47, 5965–5967; (x) A. Sasaoka, M. I. Uddin,
A. Shimomoto, Y. Ichikawa, M. Shiro and H. Kotsuki, Tetrahedron:
Asymmetry, 2006, 17, 2963–2969.
5 (a) C. Gianelli, L. Sambri, A. Carlone, G. Bartoli and P. Melchiorre,
Angew. Chem., Int. Ed., 2008, 47, 8700–8702; (b) P. Galzerano,
D. Agostino, G. Bencivenni, L. Sambri, G. Bartoli and P. Melchiorre,
Chem.–Eur. J., 2010, 16, 6069–6076; (c) T. Urushima, H. Ishikawa and
Y. Hayashi, Chem.–Eur. J., 2011, 17, 8273–8276; (d) T. Kano,
Y. Yamaguchi and K. Maruoka, Angew. Chem., Int. Ed., 2009, 48, 1838–
1840; (e) T. Kano, Y. Yamaguchi and K. Maruoka, Chem.–Eur. J., 2009,
15, 6678–6687; (f) L. Cheng, X. Han, H. Huang, M. W. Wong and Y. Lu,
Chem. Commun., 2007, 4143–4145; (g) L. Cheng, X. Wu and Y. Lu, Org.
Biomol. Chem., 2007, 5, 1018–1020; (h) E. Gómez-Bengoa, M. Maestro,
A. Mielgo, I. Otazo, C. Palomo and I. Velilla, Chem.–Eur. J., 2010, 16,
5333–5342; (i) S. S. V. Ramasastry, H. Zhang, F. Tanaka and C. F. Barbas
III, J. Am. Chem. Soc., 2007, 129, 288–289; ( j) H. Zhang,
S. S. V. Ramasastry, F. Tanaka and C. F. Barbas III, Adv. Synth. Catal.,
2008, 350, 791–796; (k) Q.-X. Guo, H. Liu, C. Guo, S.-W. Luo, Y. Gu and
L.-Z. Gong, J. Am. Chem. Soc., 2007, 129, 3790–3791; (l) Y. M. Chuan,
G. H. Chen, J. Z. Gao, H. Zhang and Y. G. Peng, Chem. Commun., 2011,
47, 3260–3262.
This work was supported by the National Undergraduate
Innovative Test Program (091063503), the Natural Science
Foundation of China (NSFC 20872120) and the Municipal
Science Foundation of Chongqing City (CSTC, 2009BB5110).
Notes and references
1 Selected reviews on asymmetric catalytic Mannich reactions, see:
(a) R. G. Arrayás and J. C. Carretero, Chem. Soc. Rev., 2009, 38, 1940–
1948; (b) J. M. M. Verkade, L. J. C. van Hemert, P. J. L. M. Quaedflieg
and F. P. J. T. Rutjes, Chem. Soc. Rev., 2008, 37, 29–41; (c) S. Mukherjee,
J. W. Yang, S. Hoffmann and B. List, Chem. Rev., 2007, 107, 5471–5569;
(d) A. Ting and S. E. Schaus, Eur. J. Org. Chem., 2007, 5797–5815;
(e) M. M. B. Marques, Angew. Chem., Int. Ed., 2006, 45, 348–352;
(f) A. Córdova, Acc. Chem. Res., 2004, 37, 102–112; (g) W. Notz,
F. Tanaka and C. F. Barbas III, Acc. Chem. Res., 2004, 37, 580–591;
(h) S. Kobayashi and H. Ishitani, Chem. Rev., 1999, 99, 1069–1094;
(i) M. Arend, B. Westermann and N. Risch, Angew. Chem., Int. Ed., 1998,
37, 1044–1070.
2 (a) A. Córdova, W. Notz, G. Zhong, J. M. Betancort and C. F. Barbas III,
J. Am. Chem. Soc., 2002, 124, 1842–1843; (b) A. Córdova, S. Watanabe,
F. Tanaka, W. Notz and C. F. Barbas III, J. Am. Chem. Soc., 2002, 124,
1866–1867; (c) W. Notz, F. Tanaka, S. Watanabe, N. S. Chowdari,
J. M. Turner, R. Thayumanavan and C. F. Barbas III, J. Org. Chem., 2003,
68, 9624–9634; (d) S. Watanabe, A. Córdova, F. Tanaka and C. F. Barbas
III, Org. Lett., 2002, 4, 4519–4522; (e) N. S. Chowdari, J. T. Suri and
C. F. Barbas III, Org. Lett., 2004, 6, 2507–2510; (f) B. Westermann and
C. Neuhaus, Angew. Chem., Int. Ed., 2005, 44, 4077–4079;
(g) P. H.-Y. Cheong, H. Zhang, R. Thayumanavan, F. Tanaka, K. N. Houk
and C. F. Barbas III, Org. Lett., 2006, 8, 811–814; (h) N. S. Chowdari,
D. B. Ramachary and C. F. Barbas III, Synlett, 2003, 1906–1909;
(i) W. Zhuang, S. Saaby and K. A. Jørgensen, Angew. Chem., Int. Ed.,
2004, 43, 4476–4478; ( j) D. A. Yalalov, S. B. Tsogoeva, T. E. Shubina, I.
M. Martynova and T. Clark, Angew. Chem., Int. Ed., 2008, 47, 6624–
6628; (k) J. M. Janey, Y. Hsiao and J. D. Armstrong III, J. Org. Chem.,
2006, 71, 390–392; (l) I. Ibrahem, H. Sundén, P. Dziedzic, R. Rios and
A. Córdova, Adv. Synth. Catal., 2007, 349, 1868–1872;
(m) M. Amedjkouh and M. Brandberg, Chem. Commun., 2008, 3043–
3045; (n) A. J. A. Cobb, D. M. Shaw, D. A. Longbottom, J. B. Gold and
S. V. Ley, Org. Biomol. Chem., 2005, 3, 84–96; (o) A. J. A. Cobb,
D. M. Shaw and S. V. Ley, Synlett, 2004, 558–560; (p) W. Wang, J. Wang
and H. Li, Tetrahedron Lett., 2004, 45, 7243–7246.
3 (a) S. Mitsumori, H. Zhang, P. H.-Y. Cheong, K. N. Houk, F. Tanaka and
C. F. Barbas III, J. Am. Chem. Soc., 2006, 128, 1040–1041; (b) H. Zhang,
M. Mifsud, F. Tanaka and C. F. Barbas III, J. Am. Chem. Soc., 2006, 128,
9630–9631; (c) H. Zhang, S. Mitsumori, N. Utsumi, M. Imai, N. Garcia-
Delgado, M. Mifsud, K. Albertshofer, P. H.-Y. Cheong, K. N. Houk,
F. Tanaka and C. F. Barbas III, J. Am. Chem. Soc., 2008, 130, 875–886;
(d) A. Córdova and C. F. Barbas III, Tetrahedron Lett., 2002, 43, 7749–
7752; (e) T. Kano, Y. Yamaguchi, O. Tokuda and K. Maruoka, J. Am.
Chem. Soc., 2005, 127, 16408–16409; (f) T. Kano, Y. Hato, A. Yamamoto
6 (a) C. Wang, C. Yu, C. L. Liu and Y. G. Peng, Tetrahedron Lett., 2009, 50,
2363–2366; (b) Y. M. Chuan, G. H. Chen and Y. G. Peng, Tetrahedron
Lett., 2009, 50, 3054–3058.
7 X. Li, H. Deng, B. Zhang, J. Y. Li, L. Zhang, S. Z. Luo and J. P. Cheng,
Chem.–Eur. J., 2010, 16, 450–455.
3738 | Org. Biomol. Chem., 2012, 10, 3730–3738
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