呋喃的有机催化不对称氮杂傅-克烷基化反应
Organocatalytic asymmetric aza-Friedel-Crafts alkylation of furan.
作者信息
Uraguchi Daisuke, Sorimachi Keiichi, Terada Masahiro
机构信息
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
出版信息
J Am Chem Soc. 2004 Sep 29;126(38):11804-5. doi: 10.1021/ja046185h.
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 gamma-butenolid.
本文描述了一种由手性磷酸催化的新型1,2-氮杂傅克反应的不对称方法。该反应以高度对映选择性的方式为呋喃-2-基胺衍生物提供了一条原子经济的合成路线。这些产物的合成效用通过呋喃环的氧化裂解（氮杂阿赫马托维奇反应）得以展现，从而形成一种1,4-二羰基化合物，该化合物可进一步衍生化为手性γ-丁烯内酯。
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