温和的镧系元素（III）催化由2-呋喃甲醛和仲胺形成4,5-二氨基环戊-2-烯酮：一种多米诺缩合/开环/电环化过程。
Mild lanthanide(III) catalyzed formation of 4,5-diaminocyclopent-2-enones from 2-furaldehyde and secondary amines: a domino condensation/ring-opening/electrocyclization process.
作者信息
Li Sze-Wan, Batey Robert A
机构信息
Department of Chemistry, 80 St. George Street, University of Toronto, Toronto, Ontario, Canada.
出版信息
Chem Commun (Camb). 2007 Sep 28(36):3759-61. doi: 10.1039/b709337n. Epub 2007 Jul 9.
DOI:10.1039/b709337n
PMID:17851619
Abstract
Lewis acid catalyzed reaction of 2-furaldehyde and secondary amines results in the formation of 4,5-diaminocyclopent-2-enones exclusively as the trans diastereomers: computational studies support the stereochemistry of the adducts as arising from a thermal conrotatory pi4a electrocyclization of an initial ring-opened intermediate (a deprotonated Stenhouse salt).
摘要
路易斯酸催化的2-呋喃甲醛与仲胺的反应仅生成反式非对映异构体的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（去质子化的施滕豪斯盐）的热顺旋π4a电环化产生的。
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