Metal Template Assisted Proximal Arrangement of a Nucleophile and an Electrophile: Site-Selective Acylation of α-Hydroxyamides in Polyols,Organic Letters

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Metal Template Assisted Proximal Arrangement of a Nucleophile and an Electrophile: Site-Selective Acylation of α-Hydroxyamides in Polyols
Organic Letters ( IF 4.9 ) Pub Date : 2018-05-23 00:00:00 , DOI: 10.1021/acs.orglett.8b01288
Yasuhiro Nishikawa ₁ , Kohei Takemoto ₁ , Kana Matsuda ₁ , Risa Tanaka ₁ , Akira Arashima ₁ , Kanako Ito ₁ , Yuki Kamezawa ₁ , Yuna Hori ₁ , Osamu Hara ₁

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Site-selective acylation of α-hydroxyl groups in amides has been achieved in the presence of other primary hydroxyl groups with intrinsic high reactivity. In this methodology, a relatively stable pyridine aldoxime ester was exploited as an acyl donor to suppress undesired acylation. The catalytic activation of a pyridine aldoxime ester with a Lewis acid produced a cationic complex, which preferentially attracted the Lewis basic α-hydroxyamide via a template effect, to thus facilitate o-acylation.

中文翻译：

金属模板辅助亲核试剂和亲电试剂的近端排列：多元醇中α-羟基酰胺的位点选择性酰化。

在存在具有固有高反应性的其他伯羟基的情况下，已经实现了酰胺中α-羟基的位点选择性酰化。在这种方法中，相对稳定的吡啶醛肟肟被用作酰基供体，以抑制不希望的酰化反应。吡啶醛肟肟与路易斯酸的催化活化作用产生了阳离子络合物，该阳离子络合物通过模板效应优先吸引了路易斯碱性α-羟基酰胺，从而促进了o-酰化反应。

更新日期：2018-05-23

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