-
1
-
-
57149097169
-
-
For reviews, see: a
-
For reviews, see: (a) Seebach, D.; Gardiner, J. Acc. Chem. Res. 2008, 41, 1366.
-
(2008)
Acc. Chem. Res
, vol.41
, pp. 1366
-
-
Seebach, D.1
Gardiner, J.2
-
2
-
-
0035471135
-
-
(b) Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219.
-
(2001)
Chem. Rev
, vol.101
, pp. 3219
-
-
Cheng, R.P.1
Gellman, S.H.2
DeGrado, W.F.3
-
3
-
-
0037201534
-
-
For a general review of stereoselective synthesis of β-amino acids, see
-
For a general review of stereoselective synthesis of β-amino acids, see: Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991.
-
(2002)
Tetrahedron
, vol.58
, pp. 7991
-
-
Liu, M.1
Sibi, M.P.2
-
4
-
-
0036828151
-
-
A general diastereoselective enolate addition to chiral sulfinyl imines: Tang, T. P.; Ellman, J. A. J. Org. Chem. 2002, 67, 7819.
-
(a) A general diastereoselective enolate addition to chiral sulfinyl imines: Tang, T. P.; Ellman, J. A. J. Org. Chem. 2002, 67, 7819.
-
-
-
-
5
-
-
44349113514
-
-
An asymmetric Mannich-type reaction to ketone-derived N-acyl hydrazones using a stoichiometric chiral promoter: Notte, G. T, Leighton, J. L. J. Am. Chem. Soc. 2008, 130, 6676
-
(b) An asymmetric Mannich-type reaction to ketone-derived N-acyl hydrazones using a stoichiometric chiral promoter: Notte, G. T.; Leighton, J. L. J. Am. Chem. Soc. 2008, 130, 6676.
-
-
-
-
6
-
-
17644402745
-
-
A diastereoselective [3 + 2] cycloaddition to chiral substrates as an alternative method for the Mannich reaction: Fuller, A. A.; Chen, B.; Minter, A. R.; Mapp, A. K. J. Am. Chem. Soc. 2005, 127, 5376.
-
A diastereoselective [3 + 2] cycloaddition to chiral substrates as an alternative method for the Mannich reaction: Fuller, A. A.; Chen, B.; Minter, A. R.; Mapp, A. K. J. Am. Chem. Soc. 2005, 127, 5376.
-
-
-
-
7
-
-
4544387566
-
-
An organo-catalyzed asymmetric Mannich reaction between special α-ketimino esters (activated ketimines) and aldehydes; Zhuang, W, Saaby, S, Jørgensen, K. A. Angew. Chem, Int. Ed. 2004, 43, 4476
-
An organo-catalyzed asymmetric Mannich reaction between special α-ketimino esters (activated ketimines) and aldehydes; Zhuang, W.; Saaby, S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 4476.
-
-
-
-
8
-
-
0000862669
-
-
General reviews: (a) Kobayashi, S.; Ishitani, H. Chem. Rev 1999, 99, 1069.
-
General reviews: (a) Kobayashi, S.; Ishitani, H. Chem. Rev 1999, 99, 1069.
-
-
-
-
10
-
-
33846409049
-
-
Suto, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 500.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 500
-
-
Suto, Y.1
Kanai, M.2
Shibasaki, M.3
-
11
-
-
55549141880
-
-
CuOAr-catalyzed direct asymmetric Mannich reaction of ketimines was recently reported: (a) Yazaki, R.; Nitabaru, T.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2008, 130, 14477.
-
CuOAr-catalyzed direct asymmetric Mannich reaction of ketimines was recently reported: (a) Yazaki, R.; Nitabaru, T.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2008, 130, 14477.
-
-
-
-
12
-
-
24044453210
-
-
The original use of Cu-conjugated Brønsted base catalyst in direct asymmetric C-C bond-formation: Suto, Y.; Tsuji, R.; Kanai, M.; Shibasaki, M. Org. Lett. 2005, 7, 3757.
-
(b) The original use of Cu-conjugated Brønsted base catalyst in direct asymmetric C-C bond-formation: Suto, Y.; Tsuji, R.; Kanai, M.; Shibasaki, M. Org. Lett. 2005, 7, 3757.
-
-
-
-
13
-
-
0345195964
-
-
For pioneering studies on transmetalation from a silyl enolate to a copper enolate, see
-
For pioneering studies on transmetalation from a silyl enolate to a copper enolate, see: Pagenkopf, B. L.; Krüger, J.; Stojanovic, A.; Carreira, E. M. Angew. Chem., Int. Ed. 1998, 37, 3124.
-
(1998)
Angew. Chem., Int. Ed
, vol.37
, pp. 3124
-
-
Pagenkopf, B.L.1
Krüger, J.2
Stojanovic, A.3
Carreira, E.M.4
-
14
-
-
0037620632
-
-
Transmetalation from silicon enolate to copper enolate is the rate-determining step in the Cu-catalyzed aldol reaction to ketones, and therefore not very efficient: Oisaki, K, Suto, Y, Kanai, M, Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 5644
-
Transmetalation from silicon enolate to copper enolate is the rate-determining step in the Cu-catalyzed aldol reaction to ketones, and therefore not very efficient: Oisaki, K.; Suto, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 5644.
-
-
-
-
15
-
-
25444446131
-
-
This type of copper enolate formation was applied to catalytic asymmetric reductive or alkylative aldol reactions of ketones. For selected examples, see: (a) Lam, H. W, Joensuu, P. M. Org. Lett. 2005, 7, 4225
-
This type of copper enolate formation was applied to catalytic asymmetric reductive or alkylative aldol reactions of ketones. For selected examples, see: (a) Lam, H. W.; Joensuu, P. M. Org. Lett. 2005, 7, 4225.
-
-
-
-
16
-
-
33744913650
-
-
(b) Deschamp, J.; Chuzel, O.; Hannedouche, J.; Riant, O. Angew. Chem., Int. Ed. 2006, 45, 1292.
-
(2006)
Angew. Chem., Int. Ed
, vol.45
, pp. 1292
-
-
Deschamp, J.1
Chuzel, O.2
Hannedouche, J.3
Riant, O.4
-
17
-
-
33750969372
-
-
(c) Zhao, D.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 14440.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 14440
-
-
Zhao, D.1
Oisaki, K.2
Kanai, M.3
Shibasaki, M.4
-
18
-
-
34250882833
-
-
(d) Oisaki, K.; Zhao, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 7439.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 7439
-
-
Oisaki, K.1
Zhao, D.2
Kanai, M.3
Shibasaki, M.4
-
19
-
-
55549102693
-
-
(e) Lipshutz, B. H.; Amorelli, B.; Unger, J. B. J. Am. Chem. Soc. 2008, 130, 14378.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 14378
-
-
Lipshutz, B.H.1
Amorelli, B.2
Unger, J.B.3
-
20
-
-
51049123834
-
-
Reviews: f
-
Reviews: (f) Deutsch, C.; Krause, N.; Lipshutz, B. H. Chem. Rev. 2008, 108, 2916.
-
(2008)
Chem. Rev
, vol.108
, pp. 2916
-
-
Deutsch, C.1
Krause, N.2
Lipshutz, B.H.3
-
21
-
-
33846485125
-
-
(g) Rendler, S.; Oestreich, M. Angew. Chem., Int. Ed. 2007, 46, 498.
-
(2007)
Angew. Chem., Int. Ed
, vol.46
, pp. 498
-
-
Rendler, S.1
Oestreich, M.2
-
22
-
-
34848883398
-
-
Reductive Mannich reactions of aldimines: (a) Nishiyama, H.; Ishikawa, J.; Shiomi, T. Tetrahedron Lett. 2007, 48, 7841.
-
Reductive Mannich reactions of aldimines: (a) Nishiyama, H.; Ishikawa, J.; Shiomi, T. Tetrahedron Lett. 2007, 48, 7841.
-
-
-
-
25
-
-
0041382872
-
-
(d) Townes, J. A.; Evans, M. A.; Queffelec, J.; Taylor, S. J.; Morken, J. P. Org. Lett. 2002, 4, 2537.
-
(2002)
Org. Lett
, vol.4
, pp. 2537
-
-
Townes, J.A.1
Evans, M.A.2
Queffelec, J.3
Taylor, S.J.4
Morken, J.P.5
-
26
-
-
0036260038
-
-
Extension to the catalytic asymmetric version has not been reported
-
(e) Muraoka, T.; Kamiya, S.; Matsuda, I.; Itoh, K. Chem. Commun. 2002, 1284. Extension to the catalytic asymmetric version has not been reported.
-
(2002)
Chem. Commun
, pp. 1284
-
-
Muraoka, T.1
Kamiya, S.2
Matsuda, I.3
Itoh, K.4
-
27
-
-
57149088362
-
-
For the initial stage optimization, see Table S-1 in Supporting Information (SI). N-Phosphinoyl ketimines produced more promising results than N-benzyl and N-toluenesulfonyl ketimines.
-
For the initial stage optimization, see Table S-1 in Supporting Information (SI). N-Phosphinoyl ketimines produced more promising results than N-benzyl and N-toluenesulfonyl ketimines.
-
-
-
-
28
-
-
33745033537
-
-
Wada, R.; Shibuguchi, T.; Makino, S.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 7687.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 7687
-
-
Wada, R.1
Shibuguchi, T.2
Makino, S.3
Oisaki, K.4
Kanai, M.5
Shibasaki, M.6
-
29
-
-
57149116026
-
-
For determination of the relative and absolute configuration of the products, see SI
-
For determination of the relative and absolute configuration of the products, see SI.
-
-
-
-
30
-
-
57149114009
-
-
There was no simple and general catalytic method for diastereoselective synthesis of β2,3,3-amino acid derivatives, even in a racemic system
-
2,3,3-amino acid derivatives, even in a racemic system.
-
-
-
-
31
-
-
57149091238
-
-
3SiH (0°C). This sharp difference might be due to switching of the reactive nucleophile (achiral boron enolate vs. chiral copper enolate) depending on the reducing reagents (see SI). The fact that enantiomeric excess of 3ba improved to 56% ee in the presence of pyridine (1.8 equiv: possible deactivator of boron enolate) using PinBH supports this consideration.
-
3SiH (0°C). This sharp difference might be due to switching of the reactive nucleophile (achiral boron enolate vs. chiral copper enolate) depending on the reducing reagents (see SI). The fact that enantiomeric excess of 3ba improved to 56% ee in the presence of pyridine (1.8 equiv: possible deactivator of boron enolate) using PinBH supports this consideration.
-
-
-
-
32
-
-
0347761350
-
-
Jeulin, S.; de Paule, S. D.; Ratovelomanana-Vidal, V.; Genêt, J.-P.; Champion, N.; Dellis, P. Angew. Chem., Int. Ed. 2004, 43, 320.
-
(2004)
Angew. Chem., Int. Ed
, vol.43
, pp. 320
-
-
Jeulin, S.1
de Paule, S.D.2
Ratovelomanana-Vidal, V.3
Genêt, J.-P.4
Champion, N.5
Dellis, P.6
-
33
-
-
57149118727
-
-
In Table 2, entries 6 and 7, no cyclized products such as 4bd were observed.
-
In Table 2, entries 6 and 7, no cyclized products such as 4bd were observed.
-
-
-
-
34
-
-
57149099870
-
-
See SI for more examples of product conversion
-
See SI for more examples of product conversion.
-
-
-
-
35
-
-
51049122384
-
-
Reviews of Cu-catalyzed asymmetric tetrasubstituted carbon construction, see: a
-
Reviews of Cu-catalyzed asymmetric tetrasubstituted carbon construction, see: (a) Shibasaki, M.; Kanai, M. Chem. Rev. 2008, 108, 2853.
-
(2008)
Chem. Rev
, vol.108
, pp. 2853
-
-
Shibasaki, M.1
Kanai, M.2
|