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c) Y. Sohtome, A. Tanatani, Y. Hashimoto, K. Nagasawa, Tetrahedron Lett. 2004, 45, 5589;
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36
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0009492483
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for other examples of non-stereoselective Friedel - Crafts additions to nitroalkenes, see: b) W. E. Noland, P. J. Hartman, J. Chem. Soc. 1954, 76, 3227;
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c) W. E. Noland, G. M. Christensen, G. L. Sauer, G. G. S. Dutton, J. Chem. Soc. 1955, 77, 456;
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and references therein
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d) M. Bandini, P. Melchiorre, A. Melloni, A. Umani-Ronchi, Synthesis 2002, 1110, and references therein.
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Synthesis
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Thieme, New York, 4th ed.
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For leading references see: A. Kleeman, J. Engel, B. Kutscher, D. Reichert, Pharmaceutical Substances, Thieme, New York, 4th ed., 2001.
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Pharmaceutical Substances
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43
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27144505836
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note
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An alkyl substituent on the indolic nitrogen atom is not tolerated in this catalytic enantioselective reaction, as the addition of N-methylindole to 3a catalyzed by 1d gave the product in good yield (75%) but in a nearly racemic form (6% ee) under the optimized reaction conditions.
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44
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27144524309
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note
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The yield of the Friedel-Crafts alkylation of 2a with 3e could be considerably increased by simply performing the reaction at higher temperatures, and only a moderate loss of enantioselectivity in the product 4h occurs (0°C, 76% yield, 72% ee).
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47
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0038025234
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