a
Table 4 Variation of nucleophiles
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4
5
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6
7
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b
c
d
Product
4
Time
Yield (%) ee
(dr)
d
Entry Nucleophile
1
(min)
(%)
8 R. Thorwirth, A. Stolle, B. Ondruschka, A. Wild and U. S. Schubert,
Chem. Commun., 2011, 47, 4370–4372.
4a
4b
4c
4d
4e
4f
10
90
99
99
9 R. Schmidt, R. Thorwirth, T. Szuppa, A. Stolle, B. Ondruschka and
H. Hopf, Chem.–Eur. J., 2011, 17, 8129–8138.
1
.6 : 1
10 R. Thorwirth, A. Stolle and B. Ondruschka, Green Chem., 2010, 12,
2
3
4
5
6
5
99
99
985–991.
11 D. A. Fulmer, W. C. Shearouse, S. T. Medonza and J. Mack, Green
Chem., 2009, 11, 1821–1825.
1
2 F. Schneider, T. Szuppa, A. Stolle, B. Ondruschka and H. Hopf, Green
Chem., 2009, 11, 1894–1899.
3 F. Schneider, A. Stolle, B. Ondruschka and H. Hopf, Org. Process Res.
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4 F. Schneider and B. Ondruschka, ChemSusChem, 2008, 1, 622–625.
5 S. Toma, R. Sebesta and M. Meciarova, Curr. Org. Chem., 2011, 15,
25
30
50
20
90
93
1
91
1
1
2
257–2281.
6 A. Bruckmann, A. Krebs and C. Bolm, Green Chem., 2008, 10, 1131–
141.
96
85
1
1
1
7 B. Rodríguez, T. Rantanen and C. Bolm, Angew. Chem., Int. Ed., 2006,
45, 6924–6926.
96
92
18 B. Rodríguez, A. Bruckmann and C. Bolm, Chem.–Eur. J., 2007, 13,
710–4722.
9 J. G. Hernández and E. Juaristi, Tetrahedron, 2011, 67, 6953–6959.
20 J. G. Hernández and E. Juaristi, J. Org. Chem., 2011, 76, 1464–1467.
4
1
a
Reactions were carried out with 2a (8.00 mmol), 1 (2.0 equiv.) and
catalyst IIIg (0.5 mol%); ball-milling conditions: 5 min at 400 rpm, and
min pause. Time for milling. Isolated yields. Determined by
2
1 J. G. Hernández, V. García-López and E. Juaristi, Tetrahedron, 2012, 68,
92–97.
2 A. Bañón-Caballero, G. Guillena and C. Nájera, Green Chem., 2010, 12,
b
c
2
2
HPLC analysis using a chiral stationary phase.
1599–1606.
2
2
3 T. Steiner, Angew. Chem., Int. Ed., 2002, 41, 48–76.
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Notes and references
25 J. P. Malerich, K. Hagihara and V. H. Rawal, J. Am. Chem. Soc., 2008,
1
A. Berkessel and H. Gröger, Asymmetric Organocatalysis, Wiley VCH,
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P. I. Dalko, Enantioselective Organocatalysis, Wiley-VCH, Weinheim, 2007.
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26 H. Y. Bae, S. Some, J. S. Oh, Y. S. Lee and C. E. Song, Chem. Commun.,
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2
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