-
1
-
-
0001141046
-
-
a) M. Arend, B. Westermann, N. Risch, Angew. Chem. 1998, 110, 1096-1122;
-
(1998)
Angew. Chem.
, vol.110
, pp. 1096-1122
-
-
Arend, M.1
Westermann, B.2
Risch, N.3
-
2
-
-
0032482080
-
-
Angew. Chem. Int. Ed. 1998, 37, 1044-1070;
-
(1998)
Angew. Chem. Int. Ed.
, vol.37
, pp. 1044-1070
-
-
-
3
-
-
0000733768
-
-
(Eds.: B. M. Trost, I. Fleming), Pergamon, New York, Chap. 4.1
-
b) E. F. Kleinmann in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991, Chap. 4.1.
-
(1991)
Comprehensive Organic Synthesis
, vol.2
-
-
Kleinmann, E.F.1
-
4
-
-
10844266525
-
-
(Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin
-
For reviews on Mannich reactions with preformed enolates see: a) S. Kobayashi, M. Ueno in Comprehensive Asymmetric Catalysis, Supplement, Vol. 1 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 2004, pp. 143-150;
-
(2004)
Comprehensive Asymmetric Catalysis, Supplement
, vol.1
, pp. 143-150
-
-
Kobayashi, S.1
Ueno, M.2
-
6
-
-
0001059120
-
-
(Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin
-
c) S. E. Denmark, O. J.-C. Nicaise in Comprehensive Asymmetric Catalysis, Vol. 2 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 923-961;
-
(1999)
Comprehensive Asymmetric Catalysis
, vol.2
, pp. 923-961
-
-
Denmark, S.E.1
Nicaise, O.J.-C.2
-
7
-
-
1642415515
-
-
for direct Mannich reactions, see: d) A. Córdova, Acc. Chem. Res. 2004, 37, 102-112;
-
(2004)
Acc. Chem. Res.
, vol.37
, pp. 102-112
-
-
Córdova, A.1
-
8
-
-
3242668608
-
-
e) S. Matsunaga, T. Yoshida, H. Morimoto, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 8777-8785;
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 8777-8785
-
-
Matsunaga, S.1
Yoshida, T.2
Morimoto, H.3
Kumagai, N.4
Shibasaki, M.5
-
9
-
-
0037495950
-
-
f) M. Marigo, A. Kjærsgaard, K. Juhl, N. Gathergood, K. A. Jørgensen, Chem. Eur. J. 2003, 9, 2359-2367;
-
(2003)
Chem. Eur. J.
, vol.9
, pp. 2359-2367
-
-
Marigo, M.1
Kjærsgaard, A.2
Juhl, K.3
Gathergood, N.4
Jørgensen, K.A.5
-
11
-
-
0000119848
-
-
h) K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem. 2001, 113, 3083-3085;
-
(2001)
Angew. Chem.
, vol.113
, pp. 3083-3085
-
-
Juhl, K.1
Gathergood, N.2
Jørgensen, K.A.3
-
12
-
-
0035902842
-
-
Angew. Chem. Int. Ed. 2001, 40, 2995-2997.
-
(2001)
Angew. Chem. Int. Ed.
, vol.40
, pp. 2995-2997
-
-
-
13
-
-
11144263200
-
-
For general reviews on organocatalysis, see: a) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248-5286;
-
(2004)
Angew. Chem.
, vol.116
, pp. 5248-5286
-
-
Dalko, P.I.1
Moisan, L.2
-
14
-
-
6044269452
-
-
Angew. Chem. Int. Ed. 2004, 43, 5138-5175;
-
(2004)
Angew. Chem. Int. Ed.
, vol.43
, pp. 5138-5175
-
-
-
18
-
-
0035886887
-
-
Angew. Chem. Int. Ed. 2001, 40, 3726-3748.
-
(2001)
Angew. Chem. Int. Ed.
, vol.40
, pp. 3726-3748
-
-
-
19
-
-
5144229459
-
-
a) W. Notz, S.-I. Watanabe, N. S. Chowdari, G. Zhong, J. M. Betancort, F. Tanaka, C. F. Barbas III, Adv. Synth. Catal. 2004, 346, 1131-1140;
-
(2004)
Adv. Synth. Catal.
, vol.346
, pp. 1131-1140
-
-
Notz, W.1
Watanabe, S.-I.2
Chowdari, N.S.3
Zhong, G.4
Betancort, J.M.5
Tanaka, F.6
Barbas III, C.F.7
-
20
-
-
6044275674
-
-
b) W. Zhuang, S. Saaby, K. A. Jørgensen, Angew. Chem. 2004, 116, 4576-4578;
-
(2004)
Angew. Chem.
, vol.116
, pp. 4576-4578
-
-
Zhuang, W.1
Saaby, S.2
Jørgensen, K.A.3
-
21
-
-
4544387566
-
-
Angew. Chem. Int. Ed. 2004, 43, 4476-4478;
-
(2004)
Angew. Chem. Int. Ed.
, vol.43
, pp. 4476-4478
-
-
-
22
-
-
4043170073
-
-
c) N. S. Chowdari, J. T. Suri, C. F. Barbas III, Org. Lett. 2004, 6, 2507-2510;
-
(2004)
Org. Lett.
, vol.6
, pp. 2507-2510
-
-
Chowdari, N.S.1
Suri, J.T.2
Barbas III, C.F.3
-
24
-
-
0345529038
-
-
e) W. Notz, F. Tanaka, S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624-9634;
-
(2003)
J. Org. Chem.
, vol.68
, pp. 9624-9634
-
-
Notz, W.1
Tanaka, F.2
Watanabe, S.3
Chowdari, N.S.4
Turner, J.M.5
Thayumanavan, R.6
Barbas III, C.F.7
-
25
-
-
1542352879
-
-
f) Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. 2003, 115, 3805-3808;
-
(2003)
Angew. Chem.
, vol.115
, pp. 3805-3808
-
-
Hayashi, Y.1
Tsuboi, W.2
Ashimine, I.3
Urushima, T.4
Shoji, M.5
Sakai, K.6
-
26
-
-
0042969372
-
-
Angew. Chem. Int. Ed. 2003, 42, 3677-3680;
-
(2003)
Angew. Chem. Int. Ed.
, vol.42
, pp. 3677-3680
-
-
-
27
-
-
0037028990
-
-
g) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866;
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 1866
-
-
Córdova, A.1
Notz, W.2
Zhong, G.3
Betancort, J.M.4
Barbas III, C.F.5
-
28
-
-
0037028924
-
-
h) A. Córdova, F. Watanabe; S. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843;
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 1842-1843
-
-
Córdova, A.1
Watanabe, F.2
Tanaka, S.3
Notz, W.4
Barbas III, C.F.5
-
29
-
-
0037028550
-
-
i) B. List, P. Porjarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827-833;
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 827-833
-
-
List, B.1
Porjarliev, P.2
Biller, W.T.3
Martin, H.J.4
-
31
-
-
4143136647
-
-
General reviews: a) S.-K. Tian, Y. Chen, J. Hang, L. Tang, P. McDaid, L. Deng, Acc. Chem. Res. 2004, 37, 621-631;
-
(2004)
Acc. Chem. Res.
, vol.37
, pp. 621-631
-
-
Tian, S.-K.1
Chen, Y.2
Hang, J.3
Tang, L.4
McDaid, P.5
Deng, L.6
-
33
-
-
0041878745
-
-
S. France, D. J. Guerin, S. J. Miller, T. Lectka, Chem. Rev. 2003, 103, 2985-3012.
-
(2003)
Chem. Rev.
, vol.103
, pp. 2985-3012
-
-
France, S.1
Guerin, D.J.2
Miller, S.J.3
Lectka, T.4
-
37
-
-
18844461913
-
-
(Eds.: H.-G. Schmalz, T. Wirth), Wiley-VCH, Weinheim
-
d) C. Carter, A. Nelson in Organic Synthesis Highlights V (Eds.: H.-G. Schmalz, T. Wirth), Wiley-VCH, Weinheim, 2003, pp. 125-133;
-
(2003)
Organic Synthesis Highlights V
, pp. 125-133
-
-
Carter, C.1
Nelson, A.2
-
39
-
-
18844451481
-
-
For recent examples, see: a) H. Li, Y. Wang, L. Tang, F. Wu, X. Liu, C. Guo, B. M. Foxman, L. Deng, Angew. Chem. 2005, 117, 107-110;
-
(2005)
Angew. Chem.
, vol.117
, pp. 107-110
-
-
Li, H.1
Wang, Y.2
Tang, L.3
Wu, F.4
Liu, X.5
Guo, C.6
Foxman, B.M.7
Deng, L.8
-
41
-
-
13444251279
-
-
b) X. Liu, H. Li, L. Deng, Org. Lett. 2005, 7, 167-169;
-
(2005)
Org. Lett.
, vol.7
, pp. 167-169
-
-
Liu, X.1
Li, H.2
Deng, L.3
-
42
-
-
8644269567
-
-
c) M. R. Acocella; O. García Mancheño, M. Bella, K. A. Jørgensen, J. Org. Chem. 2004, 69, 8165-8167;
-
(2004)
J. Org. Chem.
, vol.69
, pp. 8165-8167
-
-
Acocella, M.R.1
García Mancheño, O.2
Bella, M.3
Jørgensen, K.A.4
-
43
-
-
3042770799
-
-
d) S. Saaby, M. Bella, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 8120-8121;
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 8120-8121
-
-
Saaby, S.1
Bella, M.2
Jørgensen, K.A.3
-
45
-
-
4043154104
-
-
f) H. Li, Y. Wang, L. Tang, L. Deng, J. Am. Chem. Soc. 2004, 126, 9906-9907;
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 9906-9907
-
-
Li, H.1
Wang, Y.2
Tang, L.3
Deng, L.4
-
46
-
-
4544234565
-
-
g) P. McDaid, Y. Cheng, L. Deng, Angew. Chem. 2002, 114, 348-350;
-
(2002)
Angew. Chem.
, vol.114
, pp. 348-350
-
-
McDaid, P.1
Cheng, Y.2
Deng, L.3
-
49
-
-
0033600691
-
-
i) R. Alvarez, M.-A. Hourdin, C. Cavé, J. d'Angelo, P. Chaminade, Tetrahedron Lett. 1999, 40, 7091-7094.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 7091-7094
-
-
Alvarez, R.1
Hourdin, M.-A.2
Cavé, C.3
D'Angelo, J.4
Chaminade, P.5
-
52
-
-
0037423171
-
-
and references therein
-
For examples, see: a) R. B. Grossman, S. Comesse, R. M. Rasne, K. Hattori, M. N. Delong, J. Org. Chem. 2003, 68, 871-874, and references therein.
-
(2003)
J. Org. Chem.
, vol.68
, pp. 871-874
-
-
Grossman, R.B.1
Comesse, S.2
Rasne, R.M.3
Hattori, K.4
Delong, M.N.5
-
53
-
-
0141725892
-
-
refs. [8a,b,d]
-
For successful examples, see: b) M. S. Taylor, E. N. Jacobsen, J. Am. Chem. Soc. 2003, 125, 11204-11205; refs. [8a,b,d];
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 11204-11205
-
-
Taylor, M.S.1
Jacobsen, E.N.2
-
54
-
-
0034830057
-
-
see also: c) N. Shibata, E. Suzuki, T. Asahi, M. Shiro, J. Am. Chem. Soc. 2001, 123, 7001-7009.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 7001-7009
-
-
Shibata, N.1
Suzuki, E.2
Asahi, T.3
Shiro, M.4
-
57
-
-
0037541354
-
-
Angew. Chem. Int. Ed. 2003, 42, 1688-1690;
-
(2003)
Angew. Chem. Int. Ed.
, vol.42
, pp. 1688-1690
-
-
-
60
-
-
18844408590
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note
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Changing the imine ester group (Me, Et, nPr, iPr, tBu) gave enantioselectivities for the preferred diastereomer above 90% ee. The d.r. ranged between 80:20-89:11, the highest value having been observed for ethyl.
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-
63
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-
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The carbamate-protected imine was prepared in situ following the procedure developed by Kobayashi and co-workers; see: a) Y. Nakamura, R. Matsubara, H. Kiyohara, S. Kobayashi, Org. Lett. 2003, 5, 2481-2484;
-
(2003)
Org. Lett.
, vol.5
, pp. 2481-2484
-
-
Nakamura, Y.1
Matsubara, R.2
Kiyohara, H.3
Kobayashi, S.4
-
64
-
-
17644438939
-
-
b) S. Kobayashi, H. Kitagawa, R. Matsubara, J. Comb. Chem. 2001, 3, 401-403.
-
(2001)
J. Comb. Chem.
, vol.3
, pp. 401-403
-
-
Kobayashi, S.1
Kitagawa, H.2
Matsubara, R.3
-
65
-
-
84985239895
-
-
The synthesis and use of α-bromo glycine derivatives in the preparation of acyl α-imino esters was initially developed by Steglich and co-workers; see: c) R. Kober, W. Steglich, Liebigs Ann. Chem. 1983, 599-609;
-
(1983)
Liebigs Ann. Chem.
, pp. 599-609
-
-
Kober, R.1
Steglich, W.2
-
67
-
-
4544294700
-
-
For a discussion of the difficulties in the deprotection of tosyl amines, see: R. R. Milburn, V. Snieckus, Angew. Chem. 2004, 116, 910-912;
-
(2004)
Angew. Chem.
, vol.116
, pp. 910-912
-
-
Milburn, R.R.1
Snieckus, V.2
-
69
-
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note
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As noted (Table 2) the reactions were performed on a 0.1-mmol scale. Compound 3h was also prepared on a 0.5-mmol scale under the optimized conditions with similar results [95 % yield, 85:15 (u/l), and 95% ee].
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70
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0000803537
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The terms u (unlike) and l (like) were introduced by Seebach and Prelog as a general way of designating relative configurations in molecules with several chiral centers, particularly those in which terms like syn/anti or erythro/threo are not easily adopted; see: D. Seebach, V. Prelog, Angew. Chem. 1982, 94, 696;
-
(1982)
Angew. Chem.
, vol.94
, pp. 696
-
-
Seebach, D.1
Prelog, V.2
-
72
-
-
18844408048
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see refs. [8b,d]
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Up to 61:39 (d.r.) and up to 51 % ee. This fact has also been observed in other cinchona alkaloid-catalyzed reactions of α-substituted cyanoacetates; see refs. [8b,d].
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CCDC 260994 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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