Jung Se-Young, Min Jae-Hong, Oh Jung Taek, Koo Sangho
Department of Chemistry, Department of Nano Science and Engineering, Myong Ji University, Yongin, Kyunggi-Do, 449-728, South Korea.
J Org Chem. 2006 Jun 23;71(13):4823-8. doi: 10.1021/jo060517e.
The homoallylic alcohols 3 that can be prepared by the indium-mediated addition of haloallylic sulfones 1 to aldehydes 2 undergo the oxonia-Cope rearrangement with aldehydes 2 to give rise to the allylic sulfones 4 containing a conjugated diene moiety in a highly stereoselective manner. Electron-rich aldehydes preferentially participate in this oxonia-Cope rearrangement with the homoallylic alcohols 3. Excellent correlations of the stereochemistry (anti-3 to trans-allylic sulfone 4 and syn-3 to cis-allylic sulfone 4) have been observed in the oxonia-Cope rearrangement.
通过铟介导的卤代烯丙基砜1与醛2加成反应制备的高烯丙醇3，能与醛2发生氧杂-Cope重排反应，以高度立体选择性的方式生成含有共轭二烯部分的烯丙基砜4。富电子醛优先与高烯丙醇3参与这种氧杂-Cope重排反应。在氧杂-Cope重排反应中观察到了立体化学的良好相关性（反式-3对应反式烯丙基砜4，顺式-3对应顺式烯丙基砜4）。
