Chiral Calcium Phosphate Catalyzed Enantioselective Synthesis of All-Carbon Quaternary Center by Friedel-Crafts Alkylation Reaction of Pyrroles and Trifluoromethylated Nitrostyrenes
Chiral Calcium Phosphate Catalyzed Enantioselective Synthesis of All-Carbon Quaternary Center by Friedel-Crafts Alkylation Reaction of Pyrroles and Trifluoromethylated Nitrostyrenes
复制标题
手性磷酸钙催化吡咯与三氟甲基化硝基苯乙烯的傅克烷基化反应对映选择性合成全碳四元中心
DOI：
10.1055/s-0040-1719879
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发表时间：
2022
期刊：
影响因子：
--
通讯作者：
Murakami Mona
中科院分区：
文献类型：
--
作者：
Akiyama Takahiko;Uchikura Tatsuhiro;Yokohama Sosuke;Murakami Mona
研究了手性磷酸钙催化的吡咯与α-三氟甲基-β-硝基苯乙烯的Friedel-Crafts烷基化反应。在2-位上带有一个全碳的四元中心的吡咯具有较高的对映选择性。使用4，7-二氢吲哚作为亲核试剂和随后的氧化导致形成具有优异的对映选择性的2-取代吲哚衍生物。以3，4-二氢吡咯并[1，2-c]嘧啶为原料，经还原和苯甲酰化反应合成了3，4-二氢吡咯并[1，2-c]嘧啶衍生物。成功地实现了在1 mmol规模反应中的应用。
A chiral calcium phosphate-catalyzed enantioselective Friedel–Crafts alkylation reaction of pyrroles and α-trifluoromethyl-β-nitrostyrenes has been developed. Pyrroles bearing an all-carbon quaternary center at 2-position were obtained with high to excellent enantioselectivity. Use of 4,7-dihydroindole as a nucleophile and subsequent oxidation resulted in the formation a 2-substituted indole derivative with excellent enantioselectivity. A 3,4-dihydropyrrolo[1,2-c]pyrimidine derivative was successfully synthesized by reduction followed by benzoylation of the product without loss of enantioselectivity. Application to a 1 mmol scale reaction was successfully achieved.