Department of Chemistry , University of Torino , Via Giuria, 7 , Torino 10125 , Italy.
Org Lett. 2018 Nov 2;20(21):6891-6895. doi: 10.1021/acs.orglett.8b03026. Epub 2018 Oct 18.
An unprecedented efficient palladium(0)-catalyzed reaction of vinyl oxiranes with N-tosylhydrazones, affording "skipped" allylic alcohols in total regioselectivity and stereoselectivity, with excellent functional-group compatibility, is reported. In this Tsuji-Trost-like allylation, we propose the use of N-tosylhydrazones as a synthetic equivalent of α-styryl anions. More than 20 new products are described, including naturally occurring derivatives. A catalytic system involving an iodide (I) source is necessary to sustain the catalytic cycle.
报道了一种前所未有的钯(0)催化乙烯基环氧化合物与 N-对甲苯磺酰腙的反应，以总区域选择性和立体选择性得到“跳过”的烯丙醇，具有优异的官能团兼容性。在这种 Tsuji-Trost 型烯丙基化反应中，我们提出将 N-对甲苯磺酰腙用作α-苯乙烯基阴离子的合成等价物。描述了 20 多种新型产物，包括天然衍生产物。需要一个包含碘化物 (I) 源的催化体系来维持催化循环。
