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Versatile Scope of a Masked Aldehyde Nitrone in 1,3-Dipolar Cycloadditions
Organic Letters ( IF 4.9 ) Pub Date : 2015-11-02 00:00:00 , DOI: 10.1021/acs.orglett.5b02662
Jorin Hoogenboom 1 , Han Zuilhof 1, 2 , Tom Wennekes 1
Organic Letters ( IF 4.9 ) Pub Date : 2015-11-02 00:00:00 , DOI: 10.1021/acs.orglett.5b02662
Jorin Hoogenboom 1 , Han Zuilhof 1, 2 , Tom Wennekes 1
Affiliation
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A new masked aldehyde-containing nitrone 1 that is easily available through a facile one-step procedure has been developed. It undergoes a [3 + 2]-thermal cycloaddition with a wide range of dipolarophiles, affording isoxazolidine cycloadducts that are suitable for versatile postcycloaddition modifications. The acetal cycloadducts are acid-stable, but allow for acetal hydrolysis under mildly basic conditions. The isoxazolidine ring can be opened via an efficient one-pot procedure to give amine-protected γ-alcohols that can be further converted to furanose derivatives.
中文翻译:
1,3-偶极环加成中带掩盖的醛氮的通用范围
已经开发出一种新的含掩蔽的含醛的硝酮1,该硝酮可通过简便的一步操作轻松获得。它与多种双极性亲和剂进行[3 + 2]-热环加成反应,得到适用于多环加成后修饰的异恶唑烷环加合物。缩醛环加合物是酸稳定的,但允许在温和的碱性条件下进行缩醛水解。可以通过有效的一锅法打开异恶唑烷环,得到可以进一步转化为呋喃糖衍生物的胺保护的γ-醇。
更新日期:2015-11-02
中文翻译:
![](https://scdn.x-mol.com/jcss/images/paperTranslation.png)
1,3-偶极环加成中带掩盖的醛氮的通用范围
已经开发出一种新的含掩蔽的含醛的硝酮1,该硝酮可通过简便的一步操作轻松获得。它与多种双极性亲和剂进行[3 + 2]-热环加成反应,得到适用于多环加成后修饰的异恶唑烷环加合物。缩醛环加合物是酸稳定的,但允许在温和的碱性条件下进行缩醛水解。可以通过有效的一锅法打开异恶唑烷环,得到可以进一步转化为呋喃糖衍生物的胺保护的γ-醇。