透過亞胺葉立德前驅物與1,3-茚二酮衍生物在多樣性導向合成策略下進行 (3+2) 環加成反應生成具有位向選擇性的Chromenopyrrolidines
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2018
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I. 透過亞胺葉立德前驅物與1,3-茚二酮衍生物在多樣性導向合成策略下進行 (3+2) 環加成反應，生成具有位向選擇性的 Chromenopyrrolidines。
亞胺葉立德廣泛的應用於 (3+2) 環加成反應建構吡咯烷 (Pyrrolidine) 或是吡咯林 (Pyrroline) 等含氮五員雜環化合物，在先前的文獻中亞胺葉立德的位向選擇性通常取決於起始物的電子性質，而本次實驗利用催化劑 4-二甲氨基吡啶 (DMAP) 與四甲基胍 (TMG )建構出不同的氫鍵催化模式，形成兩種過渡態分別透過電子性質或是立體效應來主宰反應選擇性，因而造成反應物以不同位向進行(3+2) 環加成反應，亦即透過略微改變反應條件和催化劑，可成功得到兩種不同位向選擇性且具有潛在的生物活性的異構物。
I. Diversity-oriented Synthesis of Chromenopyrrolidines From azomethine Ylides and Indandionebenzylidines via regioselective (3+2) cycloaddition. Part I. Azomethine ylides are widely employed in (3+2) cycloadditions for the generation of pyrrolidines. Regioselectivity in these reactions depends mainly on the electronic properties of substrates. Our present work indicates that regioselectivity can also be influenced by reaction conditions. The same combination of starting materials could generate different chromenopyrrolidines under the influence of different bases as the catalysts activation modes. Furthermore, both the adducts obtained could serve as potential candidates for drug development due to their complex structures and combination of functional groups which are earlier shown to be bioactive sites.
I. Diversity-oriented Synthesis of Chromenopyrrolidines From azomethine Ylides and Indandionebenzylidines via regioselective (3+2) cycloaddition. Part I. Azomethine ylides are widely employed in (3+2) cycloadditions for the generation of pyrrolidines. Regioselectivity in these reactions depends mainly on the electronic properties of substrates. Our present work indicates that regioselectivity can also be influenced by reaction conditions. The same combination of starting materials could generate different chromenopyrrolidines under the influence of different bases as the catalysts activation modes. Furthermore, both the adducts obtained could serve as potential candidates for drug development due to their complex structures and combination of functional groups which are earlier shown to be bioactive sites.
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多樣性導向合成, 亞胺葉立德, 位向選擇性, (3+2) 環加成反應, 吡咯烷, 旋轉異構物, diversity-oriented synthesis, Azomethine Ylides, regioselective, (3+2) cycloaddition, Pyrrolidine, Rotamer