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首页> 外文期刊>ACS catalysis >Versatile and Enantioselective Preparation of Planar-Chiral Metallocene-Fused 4-Dialkylaminopyridines and Their Application in Asymmetric Organocatalysis
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Versatile and Enantioselective Preparation of Planar-Chiral Metallocene-Fused 4-Dialkylaminopyridines and Their Application in Asymmetric Organocatalysis

机译：平面性和对映选择性的平面性茂金属融合的4-二烷基氨基吡啶及其在不对称有机成分中的应用

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摘要

A series of ferrocene-fused planar-chiral N-tosyl-4-pyridones (S)-2b d were prepared in enantiomerically pure forms. Starting with the chiral ferrocenyl acetals, 1-[(2S,4S)-4-methoxymethyl-1,3-dioxan-2-yl]-1',2',3',4',5'-R-5-ferrocenes ((-)-3b, R = Me; (-)-3c, R = Ph; (-)-3d, R = Bn), N-tosylamino and formyl groups were introduced at the 1- and 2-positions of the ferrocene cores in (S)-11b-d with control of the planar chirality. After the reaction with ethynylmagnesium bromide, generated propargyl alcohol derivatives (S)-17 were treated with MnO2 and catalytic tetrabutylammonium iodide to give the planar-chiral pyridones by the iodide-catalyzed cyclization. This method is highly practical with a shorter and higher-yield sequence without using noble metal catalysts. Planar-chiral ferroco-pyridones (S)-2b-d were reacted with various Me3SiNR2 compounds to give a library of ferrocene-fused 4-dialkylaminopyridines ((S)-1, DAAPs) in high yields as single enantiomers by the detosylative amination. The cymantrene-fused DAAPs were also prepared in the same way. The library of chiral DAAPs was examined in the two asymmetric reactions as organocatalysts, and some newly prepared Fc-DAAPs showed better enantioselectivity than the known species.
机译：在对映体纯的形式中制备一系列二茂铁融合平面 - 手性N-酪氨基-4-吡啶酮（S）-2B D。从手性二烯基缩醛，1 - [（2S，4S）-4-甲氧基甲基-1,3-二氧-2-Y1] -1'，2'，3'，4'，5'-R-5-亚铁胶（（ - ） - 3b，r = me;（ - ） - 3c，r = pH;（ - ） - 3D，r = bn），在1-和2位引入N-甲蛋白氨基和甲酰基（s）-11b-d中的铁茂芯，控制平面手平性。在与乙炔氨基镁的反应后，用MnO 2和催化四丁基碘化物处理产生的炔丙醇衍生物-17，得到通过碘催化环化的平面 - 手性吡啶。该方法具有较短的较高和更高产量的序列，而不使用贵金属催化剂。平面性 - 手性亚硫氰酮（S）-2B-D与各种ME3SINR2化合物反应，得到二茂铁融合的4-二烷基吡啶（（S）-1，DAAPS）的文库，通过解溶化胺化为单一对映体。也以相同的方式制备CymantRene-Fused Daaps。在两种不对称的反应中检查手性Daps库，作为有机催化剂，一些新制备的Fc-Daaps显示出比已知物种更好的对映射性。

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