Page 11 of 14
Journal of the American Chemical Society
401. (d) Liu, Y.Melchiorre, P. In reference 3c, pp. 403–438. (e)
Marcantoni, E.; Petrini, M. in Amino Group Chemistry: From
Synthesis to the Life Sciences; Ricci, A., Ed.; Wiley-VCH: Weinheim,
2008, pp 93–148. (c) Roca-López, D.; Sadaba, D.; Delso, I.; Herrera,
R. P.; Tejero, T.; Merino, P. Tetrahedron: Asymmetry 2010, 21,
2562–2601.
Melchiorre, P. Angew. Chem. Int. Ed. 2012, 51, 9748–9770. (f) Niel-
sen, M.; Worgull, D.; Zweifel, T.; Gschwend, B.; Bertelsen, S.;
Jørgensen,K. A. Chem.Commun. 2011, 47, 632–649.
1
2
3
4
5
[4]
Representative examples: N-Enoyl oxazolidinones: (a)
Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325–335. (b)
Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am.
Chem. Soc. 2001, 123, 4480–4491. (c) Sibi, M. P.; Manyem, S.;
Zimmerman, J. Chem. Rev. 2003, 103, 3263–3296, and references
therein. (d) Hird, A. W.; Hoveyda, A. M. Angew. Chem. Int. Ed.
2003, 42, 1276–1279. (e) Zhuang, W.; Hazell, R. G.; Jørgensen, K. A.
Chem. Commun. 2001, 1240–1241. N-enoyl pyrazolidinones: (f) Sibi,
M. P.; Ma, Z.; Jasperse, C. P. J. Am. Chem. Soc. 2004, 126, 718–719
and references therein. N-enoyl pyrazoles: (g) Itoh, K.; Kanemasa, S.
J. Am. Chem. Soc. 2002, 124, 13394–13395. (h) Sibi, M. P.; Shay, J.
J.; Liu, M.; Jarperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615–6616.
N-acyl pyrroles: (i) Evans, D. A.; Fandrick, K. R.; Song, H.-J. J. Am.
Chem. Soc. 2005, 127, 8942–8943. (j) Matsunaga, S.; Kinoshita, T.;
Okada, S.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126,
7559–7570. -unsaturated imides: (k) Vanderwal, C. D.; Jacobsen,
E. N. J. Am. Chem. Soc. 2004, 126, 14724–14725. (l) Taylor, M. S.;
Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 11204–11205 and
references therein. (m) Sibi, M. P.; Prabagaran, N.; Ghorpade, S. G.;
Jasperse, C. P. J. Am. Chem. Soc. 2003, 125, 11796–11797. -
unsaturated acyl phosphonates: (n) Evans, D. A.; Scheidt, K. A.;
Fandrick, K. R.; Law, H. W.; Wu, J. J. Am. Chem. Soc. 2003, 125,
10780–10781. (o) Evans, D. A.; Fandrick, K. R.; Song, H.-J.; Scheidt,
K. A.; Xu, R. J. Am. Chem. Soc. 2007, 129, 10029–10041. -
unsaturated -keto esters: (p) Jensen, K. B.; Thorhauge, J.; Jørgensen,
K. A. Angew. Chem. Int.Ed. 2001, 40, 160–163. 2-acyl imidazoles:
(q) Coquière, D.; Feringa, B. L.; Roelfes, G. Angew. Chem. Int. Ed.
2007, 46, 9308–9311. (r) Evans, D. A.; Fandrick, K. R.; Song, H.-J. J.
Am. Chem. Soc. 2005, 127, 8942–8943.
[8]
Recent reviews: (a) Hong, A. Y.; Stoltz, B. M. Eur. J. Org.
Chem. 2013, 2745–2759. (b) Das, J. P.; Marek, I. Chem. Commun.,
2011, 47, 4593–4623. (c) Bella, M.; Caspery, T. Synthesis 2009,
1583–1614. (d) Cozzi, P. G.; Hilgraf, R.; Zimmerman, N. Eur. J. Org.
Chem. 2007, 5969–1614. (e) Trost, B. M.; Jiang, C. Synthesis 2006,
369–396. (f) Quaternary Stereocenters, Christoffers, J.; Baro, A.,
Eds.; Wiley-VCH: Weinheim, 2005. (g) Douglas, C. J.; Overman, L.
E. Proc. Nat. Acad. Sci. 2004, 101, 5363–5367.
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
[9]
For a review on metal-catalyzed conjugate additions lead-
ing to all-carbon quaternary stereocenters, see: Hawner, C.; Alexakis,
A. Chem. Commun. 2010, 46, 7295–7306.
[10]
Sawamura, M.; Hamashima, H.; Ito, Y. J. Am. Chem. Soc.
1992, 114, 8295–8296.
[11]
(a) Sasai, H.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc.
1994, 116, 1571–1572. (b) Sasai, H.; Emori, E.; Arai, T.; Shibasaki,
M. Tetrahedron Lett. 1996, 37, 5561–5564.
[12]
Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc.
2002, 124, 11 240–11241.
[13]
Taylor, M. S.; Zalatan, D. N.; Lerchner, A. M.; Jacobsen,
E. N. J. Am. Chem. Soc. 2005, 127, 1313–1317.
[14]
(a) Wynberg, H.; Helder, R. Tetrahedron Lett. 1975, 4057–
4060. (b) Hermann, K.; Wynberg, H. J. Org. Chem. 1979, 44, 2238–
2244.
[5]
Examples of successful bidentate templates in Brønsted
[15]
(a) Wu, F.; Li, H.; Hong, R.; Deng, L. Angew. Chem. Int.
base catalysis: N-Enoyl oxazolidinones: (a) Zu, J.; Wang, J.; Li, H.;
Xe, H.; Jiang, W.; Wang, W. J. Am. Chem. Soc. 2007, 129, 1036–
1037. N-Acyl pyrazoles and pyrazoleamides: (b) Sibi, M. P.; Itoh, K.
J. Am. Chem. Soc. 2007, 129, 8064–8065. (c) Tan, B.; Zeng, X.;
Leong, W. W. Y.; Shi, Z.; Barbas III, C.F.; Zhong, G. Chem. Eur. J.
2012, 18, 63–67. -Unsaturated imides: (d) Inokuma, T.; Hoashi,
Y.; Takemoto, Y. J. Am. Chem. Soc. 2006, 128, 9413–9419. N-Acyl
benzotriazoles: (e) Uraguchi, D.; Vek, Y.; Ooi, T. Science 2009, 326,
120–123. Acyl phosphonates: (f) Jiang, H.; Paixão, M. W.; Monge,
D.; Jørgensen, K. A. J. Am. Chem. Soc. 2010, 132, 2775–2783. (g)
Liu, T.; Wang, Y.; Wu, G.; Song, H.; Zhou, Z. ; Tang, C. J. Org.
Chem. 2011, 76, 4119–4124. Styryl isoxazoles: (h) Baschieri, A.;
Bernardi, L.; Ricci, A.; Suresh, S.; Adamo, M. F. A. Angew. Chem.
Int. Ed. 2009, 48, 9342–9345. (i) Zhang, J.; Liu, X.; Ma, X.; Wang, R.
Chem. Commun. 2013, 49, 9329–9331. 2-Oxo-3-butenoates: (j) Gao,
Y.; Ren, a.; Wang, L.; Wang, J. Chem. Eur. J. 2010, 16, 13068–
13071. (k) Xu, D.-Q.; Wang, Y.-F.; Zhang, W.; Luo, S.-P.; Zhong, A.
G.; Xia, A.-B.; Xu, Z.-Y. Chem. Eur. J. 2010, 16, 4177–4180. (l)
Basak, A. K.; Shimada, N.; Bow, W. F.; Vicic, D. A.; Tius, M. A. J.
Am. Chem. Soc. 2010, 132, 8266–8267. Thioesters and N-acryloyl
pyrrol: (m) Rigby, C. L.; Dixon, D. J. Chem. Commun. 2008, 3798–
3800. Maleimides: (n) Bartoli, G.; Bosco, M.; Carlone, A.; Cavalli,
A.; Locatelli, M.; Mazzanti, A.; Ricci, P.; Sambri, L.; Melchiorre, P.
Angew. Chem. Int. Ed. 2006, 45, 4966 –4970.
Ed. 2006, 45, 947–950. (b) Wu, F.; Li, H.; Hong, R.; Khan, J.; Liu,
X.; Deng, L. Angew. Chem. Int. Ed. 2006, 45, 4301–4305.
[16]
Reviews on Cinchona based catalysts: (a) Yeboah, E. M.
O.; Yeboah, S. O.; Sing, G. S. Tetrahedron 2011, 67, 1725–1762. (b)
Marcelli, T.; Hiemstra, H. Synthesis 2010, 1229–1279. (c) Cinchona
Alkaloids in Synthesis and Catalysis; Song, C. E., Ed.; Wiley-VCH:
Weinheim, 2009. (d) Reference 6.
[17]
(a) Brandes, S.; Niess, B.; Bella, M.; Prieto, A.; Overgaard,
J.; Jørgensen, K. A. Chem. Eur. J. 2006, 12, 6039–6052. See also: (b)
Bell, M.; Frisch, K.; Jørgensen, K. A. J. Org. Chem. 2006, 71, 5407–
5410.
[18]
Sanchez Duque, M. M.; Baslé, O.; Isambert, N.; Gaudel-
Siri, A.; Génisson, Y.; Plaquevent, J.-C.; Rodriguez, J.; Constantieux,
T. Org. Lett. 2011, 13, 3296–3299.
[19]
(a) Heathcock, C. H.; Pirrung, M. C.; Buse, C. T.; Hagen, J.
P.; Young, S. D.; Sohn, J. E. J. Am. Chem. Soc. 1979, 101, 7077–
7079. (b) Heathcock, C. H.; Pirrung, M. C.; Lampe, J.; Buse, C. T.;
Young, S. D. J. Org. Chem. 1981, 46, 2290–2300. (c) Van Draanen,
N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org.
Chem. 1991, 56, 2499–2506.
[6]
Reviews on Brønsted bases: a) Palomo, C.; Oiarbide, M.;
[20]
Diels-Alder: (a) Palomo, C.; Oiarbide, M.; García, J. M.;
López, R. Chem. Soc. Rev. 2009, 38, 632-653. (b) “Asymmetric
Organocatalysis 2, Brønsted Base and Acid Catalysis, and Additional
Topics”: Science of Synthesis; Maruoka, K., Ed.; Thieme: Stuttgart,
2012. (c) Ting, A.; Gross, J. M.; McDougal, N. T.; Schaus, S. E. Top.
Curr. Chem. 2010, 291, 145–200.
González, A.; Arceo, E. J. Am. Chem. Soc. 2003, 125, 13942–13943.
Carbamate conjugate addition: (b) Palomo, C.; Oiarbide, M.; Halder,
R.; Kelso, M.; Gómez-Bengoa, E.; García, J. M. J. Am. Chem. Soc.
2004, 126, 9188–9189. Friedel-Crafts: (c) Palomo, C.; Oiarbide, M.;
Kardak, B. G.; García, J. M.; Linden, A. J. Am. Chem. Soc. 2005, 127,
4154–4155. Nitrone cycloaddition: (d) Palomo, C.; Oiarbide, M.;
Arceo, E.; García, J. M.; López, R.; González, A.; Linden, A. Angew.
Chem. Int. Ed. 2005, 44, 6187–6190.
[7]
Reviews on nitroalkenes: (a) Berner, O. M.; Tedeschi, L.;
Enders, D. Eur. J. Org. Chem. 2002, 1877–1894. (b) Ballini, R.;
ACS Paragon Plus Environment