Zhou Gang, Corey E J
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
J Am Chem Soc. 2005 Aug 31;127(34):11958-9. doi: 10.1021/ja054503m.
A highly enantioselective [3+2]-cycloaddition reaction of 2,3-dihydrofuran with 1,4-benzoquinones using a chiral oxazaborolidinium triflimidate as catalyst has been developed which allows rapid access to a variety of chiral phenolic tricycles (enantiomeric excesses ranging from 91 to 98%). The utility of this new methodology is demonstrated by a short synthesis of the important pentacyclic natural product, aflatoxin B2. This exploratory study indicates that an even broader application of these catalysts to enantioselective cycloadditions may be possible.
已开发出一种使用手性三氟甲磺酸氧杂硼杂环丁烷鎓作为催化剂，使2,3 - 二氢呋喃与1,4 - 苯醌发生高度对映选择性的[3 + 2]环加成反应，该反应能快速得到多种手性酚类三环化合物（对映体过量率在91%至98%之间）。通过重要的五环天然产物黄曲霉毒素B2的简短合成证明了这种新方法的实用性。这项探索性研究表明，这些催化剂在对映选择性环加成反应中的应用可能会更广泛。
Zotero 插件