Oxidation of bis-sulfinyl carbanions as the pivot of ionic/radical tandem reactions
作者:Guillaume Vincent、Saloua Cheli、Rocio Martinez Mallorquin、Adi Abramovitch、Sophie Beauvière、Catherine Gomez、Franck Brebion、Ilan Marek、Max Malacria、Jean Philippe Goddard、Louis Fensterbank
DOI:10.1016/j.crci.2015.11.012
日期:2016.3
alkylidene bis-sulfoxides proceed with high diastereoselectivity. The oxidation of the resulting carbanions with iron(III) salts induces the radical cyclizations onto alkenes with a high diastereoselectivity leading to enantiopure carbo- or heterocycles. Moreover, allylic radicals have been generated by deprotonation or [1,6]-conjugate addition from alkylidene bis-sulfoxides followed by oxidation.
摘要 各种亲核试剂如锂化氨基甲酸酯、醇盐或酯烯醇化物的 [1,4]-加成以高非对映选择性进行对映纯亚烷基双亚砜。生成的碳负离子与铁 (III) 盐的氧化诱导自由基环化到烯烃上,具有高非对映选择性,导致对映纯碳或杂环。此外,烯丙基自由基已通过去质子化或 [1,6]-共轭加成从亚烷基双亚砜随后氧化产生。