通过催化 α-亚氨基自由基中间体对β-酮羰基化合物的对映选择性脱羧基α-炔基化反应。
Enantioselective Decarboxylative α-Alkynylation of β-Ketocarbonyls via a Catalytic α-Imino Radical Intermediate.
机构信息
Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences , Beijing 100190, China.
University of Chinese Academy of Sciences , Beijing 100490, China.
出版信息
Org Lett. 2017 Sep 15;19(18):4924-4927. doi: 10.1021/acs.orglett.7b02386. Epub 2017 Sep 6.
A distinctive aminocatalysis via α-imino radical is reported on the basis of SET oxidation of a secondary enamine. The combination of chiral primary amine catalysis and visible-light photoredox catalysis enables the enantioselective decarboxylative coupling of propiolic acid and β-ketocarbonyls to afford alkynylation adducts with high enantioselectivity. Mechanism studies indicate the reaction proceeds via an α-imino radical addition.
据报道，基于 SET 氧化二级烯胺，通过 α-亚氨基自由基实现了独特的氨基催化。手性伯胺催化与可见光光氧化还原催化的结合，使丙炔酸和β-酮羰基的对映选择性脱羧偶联反应能够以高对映选择性得到炔基加成产物。机理研究表明，反应通过α-亚氨基自由基加成进行。
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