7 P. G. Cozzi, F. Benfatti and L. Zoli, Angew. Chem., Int. Ed., 2009,
48, 1313.
8 (a) K. Wakasugi, T. Misaki, K. Yamada and Y. Tanabe, Tetrahedron
Lett., 2000, 41, 5249; (b) T. Akiyama, J. Itoh and K. Fuchibea, Adv.
Synth. Catal., 2006, 348, 999; (c) J. Huang and E. J. Corey, Org. Lett.,
2004, 6, 5027; (d) D. Enders, A. A. Narine, F. Toulgoat and
T. Bisschops, Angew. Chem., Int. Ed., 2008, 47, 5661.
9 J. W. Yang, M. T. Hechavarria Fonseca and B. List, J. Am. Chem.
Soc., 2005, 127, 15036.
10 Y. Huang, A. Walji, C. H. Larsen and D. W. C. MacMillan, J. Am.
Chem. Soc., 2005, 127, 15051.
11 M. Marigo, T. Schulte, J. Franzen and K. A. Jørgensen, J. Am.
Chem. Soc., 2005, 127, 15710.
12 (a) X. Zhang, S. Zhang and W. Wang, Angew. Chem. Int. Ed.,
2010, 49, 1481; (b) J. Wang, H. Li, H. Xie, L. Zu, X. Shen and
W. Wang, Angew. Chem., Int. Ed., 2007, 46, 9050; (c) W. Wang,
H. Li, J. Wang and L. Zu, J. Am. Chem. Soc., 2006, 128,
10354; (d) B. List, Chem. Commun., 2006, 819; (e) C. Liu,
X. Zhang, Rui. Wang and W. Wang, Org. Lett., 2010, 12, 4948;
(f) X. Companyo, A. Zea, A.-N. R. Alba, A. Mazzanti,
A. Moyanoa and R. Rios, Chem. Commun., 2010, 46, 6953;
(g) L.-S. Zu, H. Li, H.-X. Xie, J. Wang, W. Jiang, Y. Tang and
W. Wang, Angew. Chem., Int. Ed., 2007, 46, 3732; (h) D. Enders,
M. R. M. Huttl, C. Grondal and G. Raabe, Nature, 2006, 441, 861;
(i) J. L. Vicario, S. Reboredo, D. Badoa and L. Carrillo, Angew.
Chem., Int. Ed., 2007, 46, 5168; (j) C. Grondal, M. Jeanty,
D. Enders and M. R. M. Huttl, Nat. Chem., 2010, 2, 167;
(k) X. Yu and W. Wang, Org. Biomol. Chem., 2008, 6, 2037;
(l) D. Enders, C. Grondal and M. R. M. Huttl, Angew. Chem., Int.
Ed., 2007, 46, 1570; (m) B. Simmons, A. M. Walji and
D. W. C. MacMillan, Angew. Chem., Int. Ed., 2009, 48, 4349;
(n) J. Zhou, Chem.–Asian J., 2010, 5, 422.
13 (a) S.-L. You, Chem.–Asian J., 2007, 2, 820; (b) S. G. Ouellet,
A. M. Walji and D. W. C. Macmillan, Acc. Chem. Res., 2007, 40,
1327; (c) J. W. Yang, M. T. Hechavarria Fonseca and B. List,
Angew. Chem., Int. Ed., 2004, 43, 6660; (d) M. Rueping and
T. Theissmann, Chem. Sci., 2010, 1, 473.
14 (a) N. Vignola and B. List, J. Am. Chem. Soc., 2004, 126, 450;
(b) A. Fu, B. List and W. Thiel, J. Org. Chem., 2006, 71, 320;
(c) J. Lv, J. Zhang, Z. Lin and Y. Wang, Chem.–Eur. J., 2009, 15,
972; (d) I. Ibrahem, G.-L. Zhao, R. Rios, J. Vesely, H. Sunden,
P. Dziedzic and A. Cordova, Chem.–Eur. J., 2008, 14, 7867;
(e) R. Rios, H. Sunden, J. Vesely, G.-L. Zhao, P. Dziedzic and
A. Cordova, Adv. Synth. Catal., 2007, 349, 1028; (f) H. Xie, L. Zu,
H. Li, J. Wang and W. Wang, J. Am. Chem. Soc., 2007, 129, 10886;
(g) D. Enders, C. Wang and J. W. Bats, Angew. Chem., Int. Ed.,
2008, 47, 7539.
15 (a) D. A. Nicewicz and D. W. C. MacMillan, Science, 2008, 322,
77; (b) D. A. Nagib, M. E. Scott and D. W. C. MacMillan, J. Am.
Chem. Soc., 2009, 131, 10875; (c) T. D. Beeson, A. Mastracchio,
J.-B. Hong, K. Ashton and D. W. C. MacMillan, Science,
2007, 316, 582; (d) J. C. Conrad, J. Kong, B. N. Laforteza and
D. W. C. MacMillan, J. Am. Chem. Soc., 2009, 131, 11640;
(e) J. E. Wilson, A. D. Casarez and D. W. C. MacMillan,
J. Am. Chem. Soc., 2009, 131, 11332; (f) A. R. Brown,
W.-H. Kuo and E. N. Jacobsen, J. Am. Chem. Soc., 2010, 132,
9286; (g) I. Ibrahem and A. Cordova, Angew. Chem., Int. Ed.,
2006, 45, 1952; (h) E. Gomez-Bengoa, A. Landa, A. Lizarraga,
A. Mielgo, M. Oiarbide and C. Palomo, Chem. Sci., 2011,
2, 353.
16 (a) R. R. Shaikh, A. Mazzanti, M. Petrini, G. Bartoli and
P. Melchiorre, Angew. Chem., Int. Ed., 2008, 47, 8087. For two
examples of g-alkylation of aldehydes: (b) G. Bergonzini, S. Vera
and P. Melchiorre, Angew. Chem., Int. Ed., 2010, 49, 9685;
(c) J. Stiller, E. Marques-Lopez, R. P. Herrera, R. Frohlich,
C. Strohmann and M. Christmann, Org. Lett., 2010, 13, 70.
17 S.-K. Xiang, L.-H. Zhang and N. Jiao, Chem. Commun., 2009,
6487.
Scheme 2 Proposed catalytic cycle for this transformation.
with carbocation 12 to form the iminium intermediates 11. Finally,
the products 4 are produced by the hydrolysis of 11 with the
formation of the ammonium salt catalysts to complete the
catalytic cycle.
In summary, we developed a cascade enantioselective con-
jugate reduction and alkylation reaction of a,b-unsaturated
aldehydes with alcohols. In this transformation, the chiral
ammonium salt catalysts have been highly efficiently employed
playing three of kinds of catalytic functions including iminium
catalysis, enamine catalysis, and acid catalysis. The further
research is ongoing in our laboratory.
Financial support from Peking University, National Science
Foundation of China (Nos. 20702002, 20872003) and National
Basic Research Program of China (973 Program) (Grant No.
2009CB825300) are greatly appreciated.
Notes and references
1 (a) B. M. Trost, Angew. Chem., Int. Ed. Engl., 1995, 34, 259;
(b) B. M. Trost, Acc. Chem. Res., 2002, 35, 695; (c) J.-J. Cao,
F. Zhou and J. Zhou, Angew. Chem., Int. Ed., 2010, 49, 4976;
(d) T. Welton, Chem. Rev., 1999, 99, 2071; (e) J. Dupont, R. F. de
Souza and P. A. Z. Suarez, Chem. Rev., 2002, 102, 3667;
(f) V. I. Parvulescu and C. Hardacre, Chem. Rev., 2007, 107, 2615;
(g) Multicomponent Reactions, ed. J. Zhu and H. Bienayme,
Wiley-VCH, Weinheim, 2005; (h) Metal Catalyzed Cascade Reac-
tions, ed. T. J. J. Muller, Springer-Verlag, Berlin Heidelberg, 2006;
(i) Handbook of Green Chemistry-Green Catalysis, ed. P. T. Anastas
and R. H. Crabtree, Wiley-VCH, Weinheim, 2009.
2 (a) A. Erkkila, I. Majander and P. M. Pihko, Chem. Rev., 2007,
107, 5416; (b) M. Reiter, S. Torssell, S. Lee and D. W. C.
MacMillan, Chem. Sci., 2010, 1, 37.
3 S. Mukherjee, J. W. Yang, S. Hoffmann and B. List, Chem. Rev.,
2007, 107, 5471.
4 (a) B. L. Hodous and G. C. Fu, J. Am. Chem. Soc., 2002, 124,
10006; (b) S. L. Wiskur and G. C. Fu, J. Am. Chem. Soc., 2005,
127, 6176; (c) G. C. Fu, Acc. Chem. Res., 2004, 37, 542.
5 B. M. Nugent, R. A. Yoder and J. N. Johnston, J. Am. Chem. Soc.,
2004, 126, 3418.
6 (a) K. Ishihara, S. Nakagawa and A. Sakakura, J. Am. Chem. Soc.,
2005, 127, 4168; (b) M. Hatano, T. Maki, K. Moriyama,
M. Arinobe and K. Ishihara, J. Am. Chem. Soc., 2008, 130, 16858.
18 (a) L. Zhang, L. Cui, X. Li, J. Li, S. Luo and J.-P. Cheng,
Chem.–Eur. J., 2010, 16, 2045; (b) L.-W. Xu, G. Gao, F.-L. Gu,
H. Sheng, L. Li, G.-Q. Lai and J.-X. Jiang, Adv. Synth. Catal.,
2010, 352, 1441; (c) M. G. Capdevila, F. Benfatti, L. Zoli,
M. Stenta and P. G. Cozzi, Chem.–Eur. J., 2010, 16, 11237;
(d) Q.-X. Guo, Y.-G. Peng, J.-W. Zhang, L. Song, Z. Feng and
L.-Z. Gong, Org. Lett., 2009, 11, 4620.
c
This journal is The Royal Society of Chemistry 2011
Chem. Commun., 2011, 47, 5007–5009 5009