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手性2H-吡咯类化合物是有机合成中一类重要的合成中间体.通过催化不对称去芳构化反应,可以实现直接由吡咯类化合物来构建这类骨架.然而,目前文献上报道的对取代吡咯类化合物的直接催化去芳构化反应主要集中在过渡金属催化的不对称[4+3]环加成反应和氢化反应.由于反应过程中可能面临的化学选择性、区域选择性和对映选择性等挑战性问题,通过烷基化反应来实现吡咯环的分子间不对称去芳构化反应迄今还没有被报道.中国科学院上海有机化学研究所游书力课题组成功地通过使用烯丙基取代反应实现了取代吡咯的分子间催化不对称去芳构化.使用取代的吡咯化合物1和烯丙基碳酸酯2在金属钯和商业可得的手性配体(R)-segphos的作用下,可以以高达>
Chiral 2H-pyrrole compounds are a kind of important synthetic intermediates in organic synthesis, which can be directly constructed from pyrrole compounds by catalyzing the asymmetric aromatization reaction.However, the reports reported in the literature The direct catalytic de-aromatization reactions of substituted pyrrole compounds mainly focus on the transition metal-catalyzed asymmetric [4 + 3] cycloaddition reaction and hydrogenation reaction. Due to the chemical selectivity, regioselectivity and Asymmetric dearomatization reaction of pyrrole ring by alkylation reaction has not been reported until now.University of Shanghai for Advanced Research on Organic Chemistry, Chinese Academy of Sciences successfully translated the allyl The substitution reaction led to the asymmetric dearomatization of the substituted pyrrole by the intermolecular catalysis.Using the substituted pyrrole compound 1 and allyl carbonate 2 under the action of palladium metal and commercially available chiral ligand (R) -segphos , Can be up to>