Catalytic Asymmetric Direct-Type 1,4-Addition Reactions of Simple Amides,Journal of the American Chemical Society

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Catalytic Asymmetric Direct-Type 1,4-Addition Reactions of Simple Amides
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2015-03-26 , DOI: 10.1021/jacs.5b01943
Hirotsugu Suzuki ₁ , Io Sato ₁ , Yasuhiro Yamashita ₁ , Shu̅ Kobayashi ₁

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The development of catalytic asymmetric direct-type reactions of less acidic carbonyl compounds such as amides and esters has been a challenging theme in organic chemistry for decades. Here we describe the asymmetric direct 1,4-addition reactions of simple amides with α,β-unsaturated carbonyl compounds using a catalytic amount of a novel chiral catalyst consisting of a potassium base and a macrocyclic chiral crown ether. The desired 1,5-dicarbonyl compounds were obtained in high yields with excellent diastereo- and enantioselectivities. This is the first example of a highly enantioselective catalytic direct-type reaction of simple amides. In addition, the structure of the chiral potassium catalyst has been investigated by X-ray crystallographic, dynamic (1)H NMR, and MALDI-TOF MS analyses.

中文翻译：

简单酰胺的催化不对称直接型 1,4-加成反应

几十年来，低酸性羰基化合物（如酰胺和酯）的催化不对称直接型反应的发展一直是有机化学中的一个具有挑战性的主题。在这里，我们描述了使用催化量的由钾碱和大环手性冠醚组成的新型手性催化剂，简单酰胺与 α,β-不饱和羰基化合物的不对称直接 1,4-加成反应。以高产率获得了所需的 1,5-二羰基化合物，并具有出色的非对映选择性和对映选择性。这是简单酰胺的高度对映选择性催化直接型反应的第一个例子。此外，还通过 X 射线晶体学、动态 (1) H NMR 和 MALDI-TOF MS 分析研究了手性钾催化剂的结构。

更新日期：2015-03-26

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