Tuning Vinylethylene Carbonates into [4 + 2] Cycloaddition via Silylation and Vinylogous Peterson Elimination
作者:Wei Feng、Li Xu、Deng-Yuan Li、Pei-Nian Liu
DOI:10.1021/acs.orglett.0c01690
日期:2020.7.2
Vinylethylene carbonates have been extensively used to trigger [3 + n] or [5 + n] cycloaddition via the formation of η3-allylic intermediates, while the important [4 + n] cycloaddition has not been explored yet. Here, we report a new strategy to convert vinylethylene carbonates into 4-(trimethylsilyl)but-2-en-1-ols, which can readily undergo [4 + 2] cycloaddition by in situ formation of 1,3-dienes
碳酸乙烯基亚碳酸盐已经被广泛地用于触发[3 + Ñ ]或[5 + Ñ ]环加成经由的η形成3 -烯丙基中间体,而重要的[4 + Ñ ]环加成尚未探索尚未。在这里,我们报告了一种新的策略,将碳酸乙烯基亚乙酯转化为4-(三甲基甲硅烷基)but-2-en-1-ols,可以通过原位形成1,3-二烯容易地进行[4 + 2]环加成反应。这种新颖的反应包括[Pd II ]催化的脱羧甲硅烷基化,[Fe III ]催化的乙烯基彼得森消除,以及随后的[4 + 2]环加成反应,以提供多取代的环己-1,4-二烯骨架。