Ye Yang, Qi Xiang, Xu Bing, Lin Ying, Xiang Huan, Zou Liang, Ye Xiang-Yang, Xie Tian
School of Pharmacy, Hangzhou Normal University Hangzhou Zhejiang 311121 PR China
Key Laboratory of Elemene Class Anti-Cancer Chinese Medicines, Engineering Laboratory of Development and Application of Traditional Chinese Medicines, Collaborative Innovation Center of Traditional Chinese Medicines of Zhejiang Province, Hangzhou Normal University Hangzhou Zhejiang 311121 PR China.
Chem Sci. 2022 May 12;13(23):6959-6966. doi: 10.1039/d2sc02054h. eCollection 2022 Jun 15.
Herein, we present a facile and efficient allylation method Ni-catalyzed cross-electrophile coupling of readily available allylic acetates with a variety of substituted alkenyl bromides using zinc as the terminal reductant. This Ni-catalyzed modular approach displays excellent functional group tolerance and a broad substrate scope, which the creation of a series of 1,4-dienes including several structurally complex natural products and pharmaceutical motifs. Moreover, the coupling strategy has the potential to realize enantiomeric control. The practicality of this transformation is demonstrated through the potent modification of the naturally antitumor active molecule β-elemene.
在此，我们展示了一种简便高效的烯丙基化方法，即使用锌作为终端还原剂，通过镍催化易得的烯丙基乙酸酯与各种取代的烯基溴进行交叉亲电偶联。这种镍催化的模块化方法具有出色的官能团耐受性和广泛的底物范围，可用于构建一系列1,4 - 二烯，包括几种结构复杂的天然产物和药物基序。此外，该偶联策略具有实现对映体控制的潜力。通过对天然抗肿瘤活性分子β-榄香烯的有效修饰，证明了这种转化的实用性。
