Mild lanthanide(III) catalyzed formation of 4,5-diaminocyclopent-2-enones from 2-furaldehyde and secondary amines: a domino condensation/ring-opening/electrocyclization process
Mild lanthanide(III) catalyzed formation of 4,5-diaminocyclopent-2-enones from 2-furaldehyde and secondary amines: a domino condensation/ring-opening/electrocyclization process
复制标题
DOI：
10.1039/b709337n
复制
发表时间：
2007-01-01
影响因子：
4.9
通讯作者：
Batey, Robert A.
中科院分区：
文献类型：
--
作者：
Li, Sze-Wan;Batey, Robert A.
2-糠醛和仲胺的路易斯酸催化反应导致仅形成反式非对映异构体 4,5-二氨基环戊-2烯酮：计算研究支持加合物的立体化学是由初始开环中间体（去质子化的斯滕豪斯盐）的热旋转 pi 4a 电环化产生的。
Lewis acid catalyzed reaction of 2-furaldehyde and secondary amines results in the formation of 4,5-diaminocyclopent-2enones exclusively as the trans diastereomers: computational studies support the stereochemistry of the adducts as arising from a thermal conrotatory pi 4a electrocyclization of an initial ring-opened intermediate (a deprotonated Stenhouse salt).