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·1944·                            精细化工   FINE CHEMICALS                                 第 38 卷

            位存在取代基时,由于空间位阻的影响,收率均高                             合物的合成途径。未来可在本文的基础上采用手性
            于Ⅲa 与Ⅴa 生成Ⅵa(85%)的模板反应。并且Ⅵe                        磷酸为催化剂进一步探索底物范围,用以合成具有
            收率高于Ⅵd,可知亚胺上存在吸电子基团时更有利                            药理活性的手性产物。
            于反应的进行。
                                                               参考文献:
            2.3   反应机理推测
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            0.0025 mmol,无水 DCM(1 mL)为溶剂的条件下,                       Thiazolidine-2-thione directed diastereoselective addition of
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            室温反应 30 min,即可获得 85%收率的产物[(3-甲                         2075-2083.
            基-1H-2-吲哚基)-(苯)-甲基]氨甲酸苄酯(Ⅵa)。并                     [13]  CHENG H G, LU L Q, WANG T,  et al. Highly enantioselective
                                                                   Friedel-Crafts alkylation/N-hemiacetalization cascade reaction with
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                                                               [14]  LIU R H (刘芮含), LI H L (李红亮). Chiral  metal phosphate
                 该反应底物适用性良好,[(3,5-二甲基-1H-2-吲                       catalyzed  asymmetric reaction of 2-naphthol and imine[J]. Fine
            哚基)-(苯)-甲基]氨甲酸苄酯(Ⅵb,收率 90%)、[(3,6-                     Chemicals (精细化工), 2020, 37(9): 1940-1944.
                                                               [15]  JING H Q (荆华清), LI H L (李红亮). One-pot three-steps method
            二甲基-1H-2-吲哚基)-(苯)甲基]氨甲酸苄酯(Ⅵc,收                         for the synthesis of phenyl-2-pyridyl-methanol[J]. Fine Chemicals
            率 90%)、[(3-甲基-1H-2-吲哚基)-(4-甲基苯)-甲基]                    (精细化工), 2020, 37(10): 2150-2153.
                                                               [16]  ZHANG K F, NIE J, GUO R, et al. Chiral phosphoric acid-catalyzed
            氨甲酸苄酯(Ⅵd,收率 87%)、[(3-甲基-1H-2-吲哚                        asymmetric aza-Friedel-Crafts reaction of indoles with cyclic N-acylketimines:
            基)-(4-氯苯)-甲基]氨甲酸苄酯(Ⅵe,收率 90%)均                         Enantioselective synthesis of trifluoromethyldihydroquinazolines[J].
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            能以高收率被制备。                                          [17]  CHEN  L  Y, HE H, CHAN W H,  et al. Chiral  sulfonimide as a
                 该法直接高效、室温下反应收率良好、条件温                              Brønsted acid organocatalyst for asymmetric Friedel-Crafts alkylation
                                                                   of indoles with imines[J]. The Journal of Organic Chemistry, 2011,
            和、底物廉价易得,极大扩展了 2-吲哚甲烷胺类化                               76(17): 7141-7147.
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