Organocatalytic asymmetric aza-Friedel-Crafts alkylation of furan
Organocatalytic asymmetric aza-Friedel-Crafts alkylation of furan
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DOI：
10.1021/ja046185h
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发表时间：
2004-09-29
影响因子：
15
通讯作者：
Terada, M
中科院分区：
文献类型：
--
作者：
Uraguchi, D;Sorimachi, K;Terada, M
描述了手性磷酸催化的 1,2-aza-Friedel−Crafts 反应的新不对称进入。本反应提供了一种以高度对映选择性方式制备呋喃-2-基胺衍生物的原子经济途径。这些产品的合成效用通过呋喃环的氧化裂解（氮杂-Achmatowicz 反应）显示，形成 1,4-二羰基化合物，该化合物可以进一步衍生为手性 γ-丁烯醇。
A new asymmetric entry of the 1,2-aza-Friedel−Crafts reaction catalyzed by a chiral phosphoric acid is described. The present reaction has provided an atom-economical route to furan-2-ylamine derivatives in a highly enantioselective fashion. The synthetic utility of these products was displayed by oxidative cleavage of the furan ring (aza-Achmatowicz reaction) to form a 1,4-dicarbonyl compound that could be further derivatized to a chiral γ-butenolid.