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0037725799
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For enantioselective fluoride-mediated Henry reactions that used silyl nitronates as preactivated forms of nitroalkanes, see: a) T. Risgaard, K. V. Gothelf, K. A. Jørgensen, Org. Biomol. Chem. 2003, 1, 153-156;
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II complexes and diisopropylethylamine, see: d) Y. Kogami, T. Nakajima, T. Ashizawa, S. Kezuka, T. Ikeno, T. Yamada, Chem. Lett. 2004, 614-615;
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e) Y. Kogami, T. Nakajima, T. Ikeno, T. Yamada, Synthesis 2004, 1947-1950.
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10844258853
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For a solution to this problem within the context of the double catalytic activation strategy, see: S. Kanemasa, K. Itoh, Eur. J. Org. Chem. 2004, 4741-4753.
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27
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21244482418
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see Ref. [10b]
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Base-catalyzed, nonselective Henry reactions are long known. For the incidence of such a process in the efficiency of asymmetric catalysis, see Ref. [10b].
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28
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0037160423
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For the enolization of carbonyl compounds using metal triflates in combination with tertiary amines, see: a) D. A. Evans, J. S. Tedrow, J. T. Shaw, C. W. Downey, J. Am. Chem. Soc. 2002, 124, 392-393;
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b) D. A. Evans, C. W. Downey, J. L. Hubbs, J. Am. Chem. Soc. 2003, 125, 8706-8707;
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32
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4244117250
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II complexes in enantioselective carbonyl alkylations, see: a) K. Soai, S. Niwa, S. Chem. Rev. 1992, 92, 833-856;
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34
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0038252959
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and in carbonyl alkynylations, see: c) E. M. Carreira, Acc. Chem. Res. 2000, 33, 373-381;
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0242635970
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d) L. Pu, Tetrahedron 2003, 59, 9873-9886;
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Pu, L.1
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37
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0037078385
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II-amino-alcohol complexes have met with essentially complete failure. See: a) G. Klein, S. Pandiaraju, O. Reiser, O. Tetrahedron Lett. 2002, 43, 7503-7506;
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1442277240
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b) Y.-W. Zhong, P. Tian, G.-Q. Lin, Tetrahedron: Asymmetry 2004, 15, 771-776;
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0141730422
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Also, see Ref. [10c]
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II complexes with chiral thioaza ligands, see: c) J. Gao, A. E. Martell, Org. Biomol. Chem. 2003, 1, 2801-2806. Also, see Ref. [10c].
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Gao, J.1
Martell, A.E.2
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0037419158
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Ligand 10 was prepared by the reductive methylation of indanol. See: S. Yao, J.-C. Meng, G. Siuzdak, M. G. Finn, J. Org. Chem. 2003, 68, 2540-2546. The remaining ligands were purchased from Aldrich.
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Yao, S.1
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Finn, M.G.4
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41
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21244502829
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note
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Other combinations of metal salts and Brønsted bases were also examined, with either inferior results or complete failure of the reaction observed. See Supporting Information for more details.
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42
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21244449819
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note
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2EtN/(+)-NME (10:10:15 mol % each) led to product 3d in 75 % yield and in 90 % ee.
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43
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21244459852
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note
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Under the optimized conditions for nitromethane, the reaction between nitroethane and benzaldehyde gave a mixture of antiand syn-nitroaldols in a 65:35 ratio.
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45
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0032538773
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Angew. Chem. Int. Ed. 1998, 37, 2922-2959;
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Angew. Chem. Int. Ed.
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47
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21244448684
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note
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Similar results have also been observed in reactions with butyraldehyde and heptanal. See Supporting Information for details.
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48
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note
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[7]
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