-
2
-
-
53749099833
-
-
Special Issue on Asymmetric Organocatalysis: Acc. Chem. Res. 2004, 37, Issue 8;
-
b) Special Issue on Asymmetric Organocatalysis: Acc. Chem. Res. 2004, 37, Issue 8;
-
-
-
-
4
-
-
84891568337
-
-
J. E. Bäckvall Ed, Wiley-VCH, Weinheim
-
a) J. E. Bäckvall (Ed.), Modern Oxidation Methods, Wiley-VCH, Weinheim, 2004;
-
(2004)
Modern Oxidation Methods
-
-
-
5
-
-
20344404984
-
-
b) Q.-H. Xia, H.-Q. Ge, C.-P. Ye, Z.-M. Liu, K.-X. Su, Chem. Rev. 2005, 105, 1603.
-
(2005)
Chem. Rev
, vol.105
, pp. 1603
-
-
Xia, Q.-H.1
Ge, H.-Q.2
Ye, C.-P.3
Liu, Z.-M.4
Su, K.-X.5
-
7
-
-
0001373911
-
-
Ed, I. Ojima, VCH, Weinheim
-
b) R. A. Johnson, K. B. Sharpless in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, Weinheim, 1993, pp. 101;
-
(1993)
Catalytic Asymmetric Synthesis
, pp. 101
-
-
Johnson, R.A.1
Sharpless, K.B.2
-
8
-
-
0000345527
-
-
Eds: E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Berlin
-
c) T. Katsuki in Comprehensive Asymmetric Catalysis (Eds: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 621-648.
-
(1999)
Comprehensive Asymmetric Catalysis
, pp. 621-648
-
-
Katsuki, T.1
-
9
-
-
0000635013
-
-
Eds: E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Berlin
-
E. N. Jacobsen, M. H. Wu in Comprehensive Asymmetric Catalysis (Eds: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, vol. 2, pp. 649.
-
(1999)
Comprehensive Asymmetric Catalysis
, vol.2
, pp. 649
-
-
Jacobsen, E.N.1
Wu, M.H.2
-
10
-
-
0000450582
-
-
a) F. A. Davies, M. E. Haracal, S. B. Awad, J. Am. Chem. Soc. 1983, 105, 3123;
-
(1983)
J. Am. Chem. Soc
, vol.105
, pp. 3123
-
-
Davies, F.A.1
Haracal, M.E.2
Awad, S.B.3
-
11
-
-
33845183508
-
-
b) F. A. Davies, R. Thimma Reddy, M. C. Weismiller, J. Am. Chem. Soc. 1989, 111, 5964;
-
(1989)
J. Am. Chem. Soc
, vol.111
, pp. 5964
-
-
Davies, F.A.1
Thimma Reddy, R.2
Weismiller, M.C.3
-
12
-
-
0029617639
-
-
c) P. C. B. Page, J. P. Heer, D. Bethell, E. W. Collington, D. M. Andrews, Tetrahedron: Asymmetry 1995, 6, 2911.
-
(1995)
Tetrahedron: Asymmetry
, vol.6
, pp. 2911
-
-
Page, P.C.B.1
Heer, J.P.2
Bethell, D.3
Collington, E.W.4
Andrews, D.M.5
-
15
-
-
0027435036
-
-
a) L. Bohé, G. Hanquet, M. Lusinchi, X. Lusinchi, Tetrahedron Lett. 1993, 34, 7271;
-
(1993)
Tetrahedron Lett
, vol.34
, pp. 7271
-
-
Bohé, L.1
Hanquet, G.2
Lusinchi, M.3
Lusinchi, X.4
-
17
-
-
0007179020
-
-
c) P. C. B. Page, G. A. Rassias, D. Bethell, M. B. Schilling, J. Org. Chem. 1998, 63, 2774;
-
(1998)
J. Org. Chem
, vol.63
, pp. 2774
-
-
Page, P.C.B.1
Rassias, G.A.2
Bethell, D.3
Schilling, M.B.4
-
18
-
-
13844299492
-
-
d) P. C. B. Page, B. R. Buckley, H. Heaney, A. John Blacker, Org. Lett. 2005, 7, 375;
-
(2005)
Org. Lett
, vol.7
, pp. 375
-
-
Page, P.C.B.1
Buckley, B.R.2
Heaney, H.3
John Blacker, A.4
-
19
-
-
0037064522
-
-
e) J. Lacour, D. Monchaud, C. Marsol, Tetrahedron Lett. 2002, 43, 8257;
-
(2002)
Tetrahedron Lett
, vol.43
, pp. 8257
-
-
Lacour, J.1
Monchaud, D.2
Marsol, C.3
-
20
-
-
33846526032
-
-
f) J. Vachon, S. Rentsch, A. Martinez, C. Marsol, J. Lacour, Org. Biomol. Chem. 2007, 5, 501;
-
(2007)
Org. Biomol. Chem
, vol.5
, pp. 501
-
-
Vachon, J.1
Rentsch, S.2
Martinez, A.3
Marsol, C.4
Lacour, J.5
-
21
-
-
0001853170
-
-
g) A. Armstrong, G. Ahmed, I. Garnet, K. Goacolou, Synlett 1997, 1075.
-
(1997)
Synlett
, pp. 1075
-
-
Armstrong, A.1
Ahmed, G.2
Garnet, I.3
Goacolou, K.4
-
22
-
-
0034734309
-
-
a) M. F. A. Adamo, V. K. Aggarwal, M. A. Sage, J. Am. Chem. Soc. 2000, 122, 8317;
-
(2000)
J. Am. Chem. Soc
, vol.122
, pp. 8317
-
-
Adamo, M.F.A.1
Aggarwal, V.K.2
Sage, M.A.3
-
23
-
-
0038546766
-
-
b) V. K. Aggarwal, C. Lopin, F. Sandrinelli, J. Am. Chem. Soc. 2003, 125, 7596;
-
(2003)
J. Am. Chem. Soc
, vol.125
, pp. 7596
-
-
Aggarwal, V.K.1
Lopin, C.2
Sandrinelli, F.3
-
25
-
-
13244292377
-
-
d) C. Y. Ho, Y. C. Chen, M. K. Wong, D. Yang, J. Org. Chem. 2005, 70, 898.
-
(2005)
J. Org. Chem
, vol.70
, pp. 898
-
-
Ho, C.Y.1
Chen, Y.C.2
Wong, M.K.3
Yang, D.4
-
26
-
-
84985609389
-
-
a) S. Julià, J. Masana, J. C. Vega, Angew. Chem. Int. Ed. Engl. 1980, 19, 929;
-
(1980)
Angew. Chem. Int. Ed. Engl
, vol.19
, pp. 929
-
-
Julià, S.1
Masana, J.2
Vega, J.C.3
-
27
-
-
37049095864
-
-
b) S. Julià, J. Guixer, J. Masana, J. Rocas, S. Colonna, R. Annunziata, H. Molinari, J. Chem. Soc. Perkin Trans. 1 1982, 1317.
-
(1982)
J. Chem. Soc. Perkin Trans. 1
, pp. 1317
-
-
Julià, S.1
Guixer, J.2
Masana, J.3
Rocas, J.4
Colonna, S.5
Annunziata, R.6
Molinari, H.7
-
29
-
-
0035969617
-
-
a) A. Berkessel, N. Gasch, K. Glaubitz, C. Koch, Org. Lett. 2001, 3, 3839;
-
(2001)
Org. Lett
, vol.3
, pp. 3839
-
-
Berkessel, A.1
Gasch, N.2
Glaubitz, K.3
Koch, C.4
-
31
-
-
4644328196
-
-
c) G. Carrea, S. Colonna, A. D. Meek, G. Ottolina, S. M. Roberts, Tetrahedron: Asymmetry 2004, 15, 2945;
-
(2004)
Tetrahedron: Asymmetry
, vol.15
, pp. 2945
-
-
Carrea, G.1
Colonna, S.2
Meek, A.D.3
Ottolina, G.4
Roberts, S.M.5
-
32
-
-
27644473723
-
-
d) S. P. Mathew, S. Gunathilagan, S. M. Roberts, D. G. Blackmond, Org. Lett. 2005, 7, 4847.
-
(2005)
Org. Lett
, vol.7
, pp. 4847
-
-
Mathew, S.P.1
Gunathilagan, S.2
Roberts, S.M.3
Blackmond, D.G.4
-
33
-
-
18744407280
-
-
a) M. Marigo, G. Franzén, T. B. Poulsen, W. Zhuang, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 6964;
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 6964
-
-
Marigo, M.1
Franzén, G.2
Poulsen, T.B.3
Zhuang, W.4
Jørgensen, K.A.5
-
34
-
-
27844508553
-
-
b) W. Zhuang, M. Marigo, K. A. Jørgensen, Org. Biomol. Chem. 2005, 3, 3883;
-
(2005)
Org. Biomol. Chem
, vol.3
, pp. 3883
-
-
Zhuang, W.1
Marigo, M.2
Jørgensen, K.A.3
-
35
-
-
28544436605
-
-
c) H. Sundén, I. Ibrahem, A. Córdova, Tetrahedron Lett. 2006, 47, 99.
-
(2006)
Tetrahedron Lett
, vol.47
, pp. 99
-
-
Sundén, H.1
Ibrahem, I.2
Córdova, A.3
-
39
-
-
0346267223
-
-
D. J. Mature, T. K. Jones, L. C. Xavier, T. J. Blacklock, R. A. Reamer, J. J. Mohan, E. T. T. Turner Jones, K. Hoogsteen, M. W. Baum, E. J. J. Grabowski, J. Org. Chem. 1991, 56, 751.
-
(1991)
J. Org. Chem
, vol.56
, pp. 751
-
-
Mature, D.J.1
Jones, T.K.2
Xavier, L.C.3
Blacklock, T.J.4
Reamer, R.A.5
Mohan, J.J.6
Turner Jones, E.T.T.7
Hoogsteen, K.8
Baum, M.W.9
Grabowski, E.J.J.10
-
40
-
-
53749098601
-
-
[13c]
-
[13c]
-
-
-
-
41
-
-
33846463775
-
-
Primary amines, thanks to their reduced steric hindrance, form iminium ions more easily than secondary amines. For examples of asymmetric 1,4-addition reactions of nucleophiles to enones via iminium activation, see: a J.-W. Xie, W. Chen, R. Li, M. Zeng, W. Du, L. Yue, R. Li, Y. Wu, J. Zhu, J.-G. Deng, Angew. Chem. Int. Ed. 2007, 46, 389;
-
Primary amines, thanks to their reduced steric hindrance, form iminium ions more easily than secondary amines. For examples of asymmetric 1,4-addition reactions of nucleophiles to enones via iminium activation, see: a) J.-W. Xie, W. Chen, R. Li, M. Zeng, W. Du, L. Yue, R. Li, Y. Wu, J. Zhu, J.-G. Deng, Angew. Chem. Int. Ed. 2007, 46, 389;
-
-
-
-
42
-
-
33847051264
-
-
b) J.-W. Xie, L. Yue, W. Chen, W. Du, J. Zhu, J.-G. Deng, Org. Lett. 2007, 9, 413;
-
(2007)
Org. Lett
, vol.9
, pp. 413
-
-
Xie, J.-W.1
Yue, L.2
Chen, W.3
Du, W.4
Zhu, J.5
Deng, J.-G.6
-
43
-
-
34147174295
-
-
c) G. Bartoli, M. Bosco, A. Carlone, F. Pesciaioli, P. Ricci, L. Sambri, P. Melchiorre, Org. Lett. 2007, 9, 1403;
-
(2007)
Org. Lett
, vol.9
, pp. 1403
-
-
Bartoli, G.1
Bosco, M.2
Carlone, A.3
Pesciaioli, F.4
Ricci, P.5
Sambri, L.6
Melchiorre, P.7
-
44
-
-
33845262220
-
-
d) H. Kim, C. Yen, P. Preston, J. Chin, Org. Lett. 2006, 8, 5239.
-
(2006)
Org. Lett
, vol.8
, pp. 5239
-
-
Kim, H.1
Yen, C.2
Preston, P.3
Chin, J.4
-
46
-
-
34547202127
-
-
A. Erkkilä, P. M. Pihko, M.-R. Clarke, Adv. Synth. Catal. 2007, 349, 802.
-
(2007)
Adv. Synth. Catal
, vol.349
, pp. 802
-
-
Erkkilä, A.1
Pihko, P.M.2
Clarke, M.-R.3
-
47
-
-
53749096307
-
-
In the reaction carried out in Table 3, Entry 12, the epoxidation was not completely depressed, as part of unprotonated catalyst 11e could promote the reaction
-
In the reaction carried out in Table 3, Entry 12, the epoxidation was not completely depressed, as part of unprotonated catalyst 11e could promote the reaction.
-
-
-
-
48
-
-
53749098896
-
-
Prolonged reaction time did not improve the conversion
-
Prolonged reaction time did not improve the conversion.
-
-
-
-
50
-
-
0034698317
-
-
For a recent review on asymmetric epoxidation of electron-poor alkenes, see
-
For a recent review on asymmetric epoxidation of electron-poor alkenes, see: M. J. Porter, J. Skidmore, Chem. Commun. 2000, 1215.
-
(2000)
Chem. Commun
, pp. 1215
-
-
Porter, M.J.1
Skidmore, J.2
-
51
-
-
6344261942
-
-
a) T. Ohwada, H. Hirao, A. Ogawa, J. Org. Chem. 2004, 69, 7486;
-
(2004)
J. Org. Chem
, vol.69
, pp. 7486
-
-
Ohwada, T.1
Hirao, H.2
Ogawa, A.3
-
52
-
-
0000749388
-
-
b) M. D. Rozeboom, K. N. Houk, S. Searles, S. E. Seyedrezai, J. Am. Chem. Soc. 1982, 104, 3448.
-
(1982)
J. Am. Chem. Soc
, vol.104
, pp. 3448
-
-
Rozeboom, M.D.1
Houk, K.N.2
Searles, S.3
Seyedrezai, S.E.4
-
53
-
-
33750614288
-
-
J.-N. Li, Y. Fu, L. Liu, Q.-X. Guo, Tetrahedron 2006, 62, 11801.
-
(2006)
Tetrahedron
, vol.62
, pp. 11801
-
-
Li, J.-N.1
Fu, Y.2
Liu, L.3
Guo, Q.-X.4
-
54
-
-
53749093808
-
-
If an iminium intermediate would have been formed between secondary amines 2c and 2d and trans-chalcone, a comparable level of asymmetric induction would have been expected for the epoxide, because the side chain would have offered the same steric hindrance for the peroxide approach.
-
If an iminium intermediate would have been formed between secondary amines 2c and 2d and trans-chalcone, a comparable level of asymmetric induction would have been expected for the epoxide, because the side chain would have offered the same steric hindrance for the peroxide approach.
-
-
-
-
55
-
-
53749098745
-
-
See also Table 3, Entries 6 and 10.
-
See also Table 3, Entries 6 and 10.
-
-
-
-
56
-
-
0020767173
-
-
R. Houriet, H. Rüfenacht, P.-A. Carrupt, P. Vogel, M. Tichý, J. Am. Chem. Soc. 1983, 105, 3417.
-
(1983)
J. Am. Chem. Soc
, vol.105
, pp. 3417
-
-
Houriet, R.1
Rüfenacht, H.2
Carrupt, P.-A.3
Vogel, P.4
Tichý, M.5
-
57
-
-
53749084717
-
-
Catalyst cis-9 (Table 3, Entry 4), whose ammonium ion has a dihedral θ angle close to 0° is indeed more active than trans-10 isomer, whose ammonium ion has a dihedral θ angle bigger than 100° (Table 3, Entry 5).
-
Catalyst cis-9 (Table 3, Entry 4), whose ammonium ion has a dihedral θ angle close to 0° is indeed more active than trans-10 isomer, whose ammonium ion has a dihedral θ angle bigger than 100° (Table 3, Entry 5).
-
-
-
-
58
-
-
53749090434
-
-
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Milliam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malik, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W
-
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Milliam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malik, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision B.04, Gaussian, Pittsburgh, PA, 2003.
-
-
-
-
59
-
-
0014240342
-
-
P. S. Portoghese, T. I. Pazdernik, W. L. Kuhn, G. Hite, A. Shafi'ee, J. Med. Chem. 1968, 11, 12.
-
(1968)
J. Med. Chem
, vol.11
, pp. 12
-
-
Portoghese, P.S.1
Pazdernik, T.I.2
Kuhn, W.L.3
Hite, G.4
Shafi'ee, A.5
-
60
-
-
1842510519
-
-
a) H. L. Zhang, F. Jiang, X.-M. Zhang, X. Cui, L.-Z. Gong, A.-Q. Mi, Y.-Z. Jiang, Y.-D. Wu, Chem. Eur. J. 2004, 10, 1481;
-
(2004)
Chem. Eur. J
, vol.10
, pp. 1481
-
-
Zhang, H.L.1
Jiang, F.2
Zhang, X.-M.3
Cui, X.4
Gong, L.-Z.5
Mi, A.-Q.6
Jiang, Y.-Z.7
Wu, Y.-D.8
-
61
-
-
0028861731
-
-
b) P. Delair, C. Heinhorn, J. Heinhorn, J. L. Luche, Tetrahedron 1995, 51, 165.
-
(1995)
Tetrahedron
, vol.51
, pp. 165
-
-
Delair, P.1
Heinhorn, C.2
Heinhorn, J.3
Luche, J.L.4
-
63
-
-
0037127783
-
-
b) S. Arai, H. Tsuge, M. Oku, M. Miura, T. Shioiri, Tetrahedron 2002, 58, 1623;
-
(2002)
Tetrahedron
, vol.58
, pp. 1623
-
-
Arai, S.1
Tsuge, H.2
Oku, M.3
Miura, M.4
Shioiri, T.5
-
64
-
-
1642402312
-
-
c) B. M. Choudary, M. L. Kantam, K. V. S. Ranganath, K. Mahendar, B. Sreedhar, J. Am. Chem. Soc. 2004, 126, 3396.
-
(2004)
J. Am. Chem. Soc
, vol.126
, pp. 3396
-
-
Choudary, B.M.1
Kantam, M.L.2
Ranganath, K.V.S.3
Mahendar, K.4
Sreedhar, B.5
|