Lett., 2001, 3, 803; (e) H.-F. Duan, J.-H. Xie, W.-J. Shi, Q. Zhang
and Q.-L. Zhou, Org. Lett., 2006, 8, 1479; (f) A. F. Trindade, P. M.
P. Gois, L. F. Veiros, V. Andre, M. T. Duarte, C. A. M. Afonso,
S. Caddick and F. G. N. Cloke, J. Org. Chem., 2008, 73, 4076;
(g) P. M. P. Gois, A. F. Trindade, L. F. Veiros, V. Andre,
M. T. Duarte, C. A. M. Afonso, S. Caddick and F. G. N. Cloke,
Angew. Chem., Int. Ed., 2007, 46, 5750.
3 For examples of palladium-catalyzed addition of organoboronic
acids to aldehydes, see: (a) C. Qin, H. Wu, J. Cheng, X. Chen,
M. Liu, W. Zhang, W. Su and J. Ding, J. Org. Chem., 2007, 72,
4102; (b) T. Yamamoto, T. Ohto and Y. Ito, Org. Lett., 2005, 7,
4153; (c) P. He, Y. Lu, C.-G. Dong and Q.-S. Hu, Org. Lett., 2007,
9, 343; (d) S. Liu and X. Lu, J. Org. Chem., 2007, 72, 9757;
(e) M. Kuriyama, R. Shimazawa and R. Shirai, J. Org. Chem.,
2008, 73, 1597; (f) M. Kuriyama, R. Shimazawa, T. Enomoto and
R. Shirai, J. Org. Chem., 2008, 73, 6939.
4 For examples of other metal-catalyzed addition of organoboronic
acids to aldehydes, see: (a) Y. Yamamoto, K. Kurihara and
N. Miyaura, Angew. Chem., Int. Ed., 2009, 48, 4414;
(b) H. Zheng, Q. Zhang, J. Chen, M. Liu, S. Cheng, J.
Ding, H. Wu and W. Su, J. Org. Chem., 2009, 74, 943;
(c) Y.-X. Liao, C.-H. Xing, P. He and Q.-S. Hu, Org. Lett.,
2008, 10, 2509.
5 For transition metal-catalyzed addition of organoboronic acids to
imines, see: (a) T. Hayashi, M. Kawai and N. Tokunaga, Angew.
Chem., Int. Ed., 2004, 43, 6125; (b) R. B. C. Jagt, P. Y. Toullec,
D. Geerdink, J. G. deVries, B. L. Feringa and A. J. Minnaard,
Angew. Chem., Int. Ed., 2006, 45, 2789; (c) T. Hayashi and
M. Ishigedani, J. Am. Chem. Soc., 2000, 122, 976;
(d) M. Kuriyama, T. Soeta, X. Hao, Q. Chen and K. Tomioka,
J. Am. Chem. Soc., 2004, 126, 8128; (e) N. Tokunaga, Y. Otomaru,
K. Okamoto, K. Ueyama, R. Shintani and T. Hayashi, J. Am.
Chem. Soc., 2004, 126, 13584; (f) D. J. Weix, Y. Shi and
J. A. Ellman, J. Am. Chem. Soc., 2005, 127, 1092;
(g) M. Beenen, D. J. Weix and J. A. Ellman, J. Am. Chem. Soc.,
2006, 128, 6304; (h) Z.-Q. Wang, C.-G. Feng, M.-H. Xu and
G.-Q. Lin, J. Am. Chem. Soc., 2007, 129, 5336; (i) M. Ueda and
N. Miyaura, J. Organomet. Chem., 2000, 595, 31; (j) Y. Otomaru,
N. Tokunaga, R. Shintani and T. Hayashi, Org. Lett., 2005, 7, 307;
(k) Y. Bolshan and R. A. Batey, Org. Lett., 2005, 7, 1481;
(l) H.-F. Duan, Y.-X. Jia, L.-X. Wang and Q.-L. Zhou, Org. Lett.,
2006, 8, 2567; (m) H. Nakagawa, J. C. Rech, R. W. Sindelar and
J. A. Ellman, Org. Lett., 2007, 9, 5155; (n) H. Dai and X. Lu,
Tetrahedron Lett., 2009, 50, 3478; (o) G.-N. Ma, T. Zhang and
M. Shi, Org. Lett., 2009, 11, 875.
Chem. Soc., 2005, 127, 10323; (d) M. Nilsson, Acta Chem. Scand.,
1966, 20, 423.
8 (a) L. J. Gooben, W. R. Thiel, N. Rodrı
B. Melzer, Adv. Synth. Catal., 2007, 349, 2241; (b) L. J. Gooben,
F. Rudolphi, C. Oppel and N. Rodrıguez, Angew. Chem., Int. Ed.,
´
guez, C. Linder and
´
2008, 47, 3043; (c) L. J. Gooben, B. Zimmermann and T. Knauber,
Angew. Chem., Int. Ed., 2008, 47, 7103; (d) A. G. Myers,
D. Tanaka and M. R. Mannion, J. Am. Chem. Soc., 2002, 124,
11250; (e) D. Tanaka, S. P. Romeril and A. G. Myers, J. Am.
Chem. Soc., 2005, 127, 10323; (f) P. Forgione, M. C. Brochu,
M. St-Onge, K. H. Thesen, M. D. Bailey and F. Bilodeau, J. Am.
Chem. Soc., 2006, 128, 11350; (g) L. J. Gooben, N. Rodrı
B. Melzer, C. Linder, G. Deng and L. M. Levy, J. Am. Chem. Soc.,
2007, 129, 4824; (h) L. J. Gooben, N. Rodrıguez and C. Linder,
´
guez,
´
J. Am. Chem. Soc., 2008, 130, 15248; (i) R. Shang, Y. Fu, J.-B. Li,
S.-L. Zhang, Q.-X. Guo and L. Liu, J. Am. Chem. Soc., 2009, 131,
5738; (j) Z. Duan, S. Ranjit, P. Zhang and X. Liu, Chem.–Eur. J.,
´
2009, 15, 3666; (k) L. J. Gooben, C. Linder, N. Rodrıguez and
P. P. Lange, Chem.–Eur. J., 2009, 15, 9336; (l) L. J. Gooben,
G. Deng and L. M. Levy, Science, 2006, 313, 662.
9 (a) D. Tanaka and A. G. Myers, Org. Lett., 2004, 6, 433;
(b) J. S. Dickstein, C. A. Mulrooney, E. M. O’Brien,
B. J. Morgan and M. C. Kozlowski, Org. Lett., 2007, 9, 2441;
(c) J. Moon, M. Jeong, H. Nam, J. Ju, J. H. Moon, H. M. Jung and
S. Lee, Org. Lett., 2008, 10, 945; (d) M. Nakano, H. Tsurugi,
T. Satoh and M. Miura, Org. Lett., 2008, 10, 1851; (e) P. Hu,
J. Kan, W. Su and M. Hong, Org. Lett., 2009, 11, 2341;
(f) J.-M. Becht, C. Catala, C. L. Drian and A. Wagner, Org. Lett.,
2007, 9, 1781; (g) J.-M. Becht and C. L. Drian, Org. Lett., 2008, 10,
3161; (h) L. J. Gooben and B. Melzer, J. Org. Chem., 2007, 72,
7473; (i) J. Moon, M. Jang and S. Lee, J. Org. Chem., 2009, 74,
1403; (j) L. J. Gooben, N. Rodrıguez and K. Gooben, Angew.
´
Chem., Int. Ed., 2008, 47, 3100; (k) H. Kim and P. H. Lee, Adv.
Synth. Catal., 2009, 351, 2827; (l) L. J. Gooben, B. Zimmermann,
´
C. Linder, N. Rodrıguez, P. P. Lange and J. Hartung, Adv. Synth.
Catal., 2009, 351, 2667; (m) M. Miyasaka, K. Hirano, T. Satoh and
M. Miura, Adv. Synth. Catal., 2009, 351, 2683.
10 (a) Z. Wang, Q. Ding, X. He and J. Wu, Org. Biomol. Chem., 2009,
7, 863; (b) Z. Wang, Q. Ding, X. He and J. Wu, Tetrahedron, 2009,
65, 4635.
11 For examples, see: (a) M. J. Bishop and R. W. McNutt, Bioorg.
Med. Chem. Lett., 1995, 5, 1311; (b) C. M. Spencer, D. Foulds and
D. H. Peters, Drugs, 1993, 46, 1055; (c) S. Sakurai, N. Ogawa,
T. Suzuki, K. Kato, T. Ohashi, S. Yasuda, H. Kato and Y. Ito,
Chem. Pharm. Bull., 1996, 44, 765; (d) N. Plobeck, D. Delorme,
Z.-Y. Wei, H. Yang, F. Zhou, P. Schwarz, L. Gawell, H. Gagnon,
B. Pelcman, R. Schmidt, S.-Y. Sue, C. Walpole, W. Brown,
E. Zhou, M. Labarre, K. Payza, S. St-Onge, A. Kamassah,
P.-E. Morin and D. Projean, J. Med. Chem., 2000, 43, 3878.
6 O. Baudoin, Angew. Chem., Int. Ed., 2007, 46, 1373.
7 (a) A. G. Myers, D. Tanaka and M. R. Mannion, J. Am. Chem.
Soc., 2002, 124, 11250; (b) D. Tanaka and A. G. Myers, Org. Lett.,
2004, 6, 433; (c) D. Tanaka, S. P. Romeril and A. G. Myers, J. Am.
ꢀc
This journal is The Royal Society of Chemistry 2010
Chem. Commun., 2010, 46, 3785–3787 | 3787