Novel Carbon−Carbon Bond-Forming Reactions Using Carbocations Produced from Substituted Propargyl Silyl Ethers by the Action of TMSOTf
作者:Teruhiko Ishikawa、Masamitu Okano、Toshiaki Aikawa、Seiki Saito
DOI:10.1021/jo010157p
日期:2001.6.1
stable allenyl, propargyl, or allyl-propargyl hybrid cations have been developed. These carbocations could be generated from silyl 1-(pi-donor)-substituted propargyl ethers by the action of trimethylsilyl trifluoromethanesulfonate in dichloromethane at -78 degrees C to room temperature and could be attacked nucleophilically by electron rich arenes, allylsilanes, or enol silyl ethers, giving rise to
已经开发出使用稳定的烯基,炔丙基或烯丙基-炔丙基杂化阳离子的高度有用的碳-碳键形成反应。这些碳阳离子可能是由甲硅烷基1-(π-供体)取代的炔丙基醚在二氯甲烷中于-78摄氏度至室温下通过三氟甲磺酸三甲基甲硅烷基酯的作用而生成的,并可能被富电子的芳烃,烯丙基硅烷或烯醇甲硅烷基醚亲核攻击,会产生异戊烯,炔烃及其衍生物。还建立了利用烯丙基-炔丙基杂化阳离子进行共轭烯炔的区域和立体选择性合成的新方法。