当前位置: X-MOL 学术Tetrahedron › 论文详情
Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
Simple organocatalysts in multi-step reactions: An efficient one-pot Morita-Baylis-Hillman-type α-hydroxymethylation of vinyl ketones followed by the convenient, temperature-controlled one-pot etherification using alcohols
Tetrahedron ( IF 2.1 ) Pub Date : 2018-05-18 , DOI: 10.1016/j.tet.2018.05.026
Marvin Mantel , Marian Guder , Jörg Pietruszka

1,4-Diazabicyclo[2.2.2]octane (DABCO) was utilized as versatile catalyst in a one-pot synthesis: First, for the preparation of alcoholic formaldehyde solutions from para-formaldehyde catalysed by using low loadings of inexpensive DABCO. Second, for the fast α-hydroxymethylation of alkylic and aromatic vinyl ketones in high yields. In a third step, the same catalyst can be used for an optional, temperature controlled in situ etherification of the Morita-Baylis-Hillman product with various alcohols on a multi-gram scale in moderate to good overall yields and high purities. Furthermore, an application of the ether in the enantioselective synthesis of a common building block for total synthesis is shown, thus providing a gram-scale access from inexpensive bulk chemicals.



中文翻译:

多步骤反应中的简单有机催化剂:乙烯基酮的高效一锅森田-贝利斯-希尔曼型α-羟甲基化,然后使用醇方便地进行温度控制的一锅醚化

1,4-二氮杂双环[2.2.2]辛烷(DABCO)在单罐合成中用作通用催化剂:首先,通过使用低负荷的廉价DABCO催化从对甲醛中制备醇甲醛溶液。第二,用于烷基和芳族乙烯基酮的快速α-羟甲基化,产率高。第三步,相同的催化剂可用于Morita-Baylis-Hillman的可选的,可控温度的原位醚化产品具有多种克级数的醇,具有中等至良好的总收率和高纯度。此外,显示了醚在用于全合成的通用结构单元的对映选择性合成中的应用,从而提供了从廉价的散装化学品中获得克级的访问量。

更新日期:2018-05-18
down
wechat
bug