FAM-Ag-catalyzed asymmetric synthesis of heteroaryl-substituted pyrrolidines,Chirality

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FAM-Ag-catalyzed asymmetric synthesis of heteroaryl-substituted pyrrolidines
Chirality ( IF 2.8 ) Pub Date : 2021-05-26 , DOI: 10.1002/chir.23320
Nurzhan Beksultanova ₁ , Zeynep Gözükara ₁ , Mihrimah Araz ₁ , Merve Bulut ₁ , Sıdıka Polat-Çakır ₂ , Muhittin Aygün ₃ , Özdemir Dogan ₁

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New derivatives of FAM (ferrocenyl aziridinyl methanol) ligands NFAM1–4 (naphthyl ferrocenyl aziridinyl methanol) and CFAM1–4 (cyclohexyl ferrocenyl aziridinyl methanol) were synthesized to form a small ligand library and used as chiral catalysts with AgOAc for the asymmetric synthesis of heteroaryl-substituted pyrrolidines by the 1,3-dipolar cycloaddition (1,3-DC) reaction of azomethine ylides. 2-Thienyl, 2-furyl, 2-, 3-, and 4-pyridyl aldimines were prepared and used with N-methylmaleimide, dimethyl maleate, tert-butyl acrylate, methyl acrylate, and acrylonitrile to form the corresponding heteroaryl-substituted pyrrolidines. 1,3-DC reactions yielded the expected cycloadducts in up to 89% yield and up to 76% ee that could be increased up to 95% ee upon crystallization. New chiral ligands NFAM1–4 and CFAM1–4 were fully characterized, and their absolute stereochemistry was determined by single-crystal X-ray analysis.

中文翻译：

FAM-Ag催化杂芳基取代吡咯烷的不对称合成

合成了FAM（二茂铁基氮丙啶基甲醇）配体NFAM1-4（萘基二茂铁基氮丙啶基甲醇）和CFAM1-4（环己基二茂铁基氮丙啶基甲醇）的新衍生物以形成一个小的配体库，并用作与 AgOAc 一起不对称合成杂芳基的手性催化剂通过偶氮甲碱叶立德的 1,3-偶极环加成 (1,3-DC) 反应生成 - 取代的吡咯烷。制备了 2-噻吩基、2-呋喃基、2-、3- 和 4-吡啶基醛亚胺，并与N-甲基马来酰亚胺、马来酸二甲酯、叔丙烯酸丁酯、丙烯酸甲酯和丙烯腈形成相应的杂芳基取代的吡咯烷。1,3-DC 反应以高达 89% 的产率和高达 76% 的 ee 产生预期的环加合物，结晶后可增加高达 95% ee。新的手性配体NFAM1-4和CFAM1-4被完全表征，它们的绝对立体化学由单晶 X 射线分析确定。

更新日期：2021-07-16

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