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(e) See also: Mitsumori, S.; Zhang, H.; Cheong, P. H.-Y.; Houk, K. N.; Tanaka, F.; Barbas, C. F., III. J. Am. Chem. Soc. 2006, 128, 1040.
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(a) Asymmetric Organocatalysis; Berkessel, A.. Gröger, H., Eds.; Wiley-VCH: Weinheim, Germany, 2005; Chapter 5.2.
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(b) For a recent application in synthesis, see: Enders, D.; Grondal, C.; Vrettou, M.; Raabe, G. Angew. Chem., Int. Ed. 2005, 44, 4079.
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(c) See also: Ibrahem, I.; Zou, W.; Engqvist, M.; Xu, Y.; Córdova, A. Chem.-Eur. J. 2005, 11, 7024.
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33645520036
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note
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4, and the resulting amino alcohols 5 (obtained as syn/anti mixtures, with the latter in excess) were then analyzed. For details, see Supporting Information.
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19
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11144325118
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For recent reviews on the use of MWs in organic synthesis, see: (a) Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250.
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Kappe, C.O.1
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(b) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
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Lidström, P.1
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Tierney, J. P., Lidström, P., Eds.; Blackwell: Oxford, U.K.
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(d) Microwave Assisted Organic Synthesis; Tierney, J. P., Lidström, P., Eds.; Blackwell: Oxford, U.K., 2005.
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0011932271
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Loupy, A., Ed.; Wiley-VCH: Weinheim, Germany
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(e) Microwaves in Organic Synthesis; Loupy, A., Ed.; Wiley-VCH: Weinheim, Germany, 2002.
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33645506728
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Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany
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(f) Lee, J.; Hlasta, D. J. In Transition Metals for Organic Synthesis, 2nd ed.; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 2004; p 597.
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Lee, J.1
Hlasta, D.J.2
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0346456942
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For a study describing the effect of MW in (nonasymmetric) Mannich-type reactions catalyzed by CuCl in conjunction with an ionic liquid, see: Leadbeater, N. E.; Torenius, H. M.; Tye, H. Mol. Diversity 2003, 7, 135.
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Mol. Diversity
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Tye, H.3
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Westermann, B.; Neuhaus, C. Angew. Chem., Int. Ed. 2005, 44, 4077.
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27
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0000153467
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For an interesting study on MW-promoted reactions with supported enzymes in dry media, see: Carrillo-Muñoz, J.-R.; Bouvet, D.; Guibé-Jampel, E.; Loupy, A.; Petit, A. J. Org. Chem. 1996, 61, 7746.
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For a review on MW-accelerated homogeneous (metal) catalysis, see: Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717.
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33645511507
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note
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Unfortunately, information on the reaction temperature of the experiments performed under MW irradiation is lacking in this article. Furthermore, a comparison with conventional methods of heating has not been reported.
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For a recent excellent study of MW-assisted reactions under simultaneous cooling, see: Leadbeater, N. E.; Pillsbury, S. J.; Shanahan, E.; Williams, V. A. Tetrahedron 2005, 61, 3565.
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max = 40 °C) of the instrument. Thus, at the present stage, a reliable error margin of the given temperatures (Table 2) cannot be given. This should, however, not affect the reproducibility of the experiments. For a comparative study of temperature determinations under MW irradiations, see: Ondruschka, M. N. B.; Weiß, D.; Beckert, R.; Bonrath, W.; Gum, A. Chem. Eng. Technol. 2005, 28, 871.
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Gum, A.5
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33645508796
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note
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For comparison, the reaction between ketone 1a, formaldehyde (2a), and aniline (3a), catalyzed by 10 mol % of (S)-proline, was performed using MW irradiation without simultaneous cooling (15 W, 2.5 h; see also Table 2. entry 5). Under these conditions, the maximum temperature reached was 89 °C, and the product was obtained in just 53% yield, having an ee of 91%. (The temperature profile is included in Supporting Information).
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note
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Reactions in oil bath were performed in the 10 mL glass vessels used in the MW-assisted experiments.
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34
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Personal communication
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Analogous observations have also been made in other organocatalytic Mannich-type reactions. Kappe, C. O.; Barbieri, V. Personal communication.
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Kappe, C.O.1
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