1,3-Dipolar Cycloaddition of Fluorenethione S-Oxide and trans-Cyclooctene: Isolation of a Sultene and Its Novel Acid-Catalyzed Diastereoselective Sulfur-Atom Transfer to Cyclic Olefins
Lewis Acid Catalyzed Sulfur Transfer from a Sultene to Strained Cyclic Alkenes
作者:Waldemar Adam、Bettina Fröhling
DOI:10.1021/ol017203s
日期:2002.2.1
[GRAPHICS]Sultene 1 reacts with cyclic alkenes under mild Lewis acid catalysis to form thiiranes diastereoselectively. With 1-methoxycyclooctene as sulfur acceptor, an unexpected insertion product is formed, which provides valuable mechanistic insight into the sulfur-transfer process.
1,3-Dipolar Cycloaddition of Fluorenethione <i>S</i>-Oxide and <i>trans</i>-Cyclooctene: Isolation of a Sultene and Its Novel Acid-Catalyzed Diastereoselective Sulfur-Atom Transfer to Cyclic Olefins