Prévost Michel, Woerpel K A
Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
J Am Chem Soc. 2009 Oct 14;131(40):14182-3. doi: 10.1021/ja906204a.
This communication describes a direct route to functionalized nonracemic trans-dioxasilacyclooctenes that involves stereoselective silylene insertions into vinyl epoxides to provide vinyl silaoxetane intermediates. These strained allylic silanes then undergo uncatalyzed allylation of aldehydes to afford trans-dioxasilacyclooctenes. Diastereoselective additions to these alkenes allow efficient transfer of planar chirality to chirality at stereogenic carbon atoms.
本通讯描述了一种合成官能化非外消旋反式二氧杂硅杂环辛烯的直接方法，该方法涉及硅烯对环氧乙烯进行立体选择性插入反应，以提供乙烯基硅杂环丁烷中间体。这些具有张力的烯丙基硅烷随后在无催化条件下与醛发生烯丙基化反应，生成反式二氧杂硅杂环辛烯。对这些烯烃进行非对映选择性加成反应，可实现平面手性向立体中心碳原子手性的高效转移。
