Choudhury Partha P, Welker Mark E
Department of Chemistry, Wake Forest University, P. O. Box 7486, Winston-Salem, NC 27109, USA.
Molecules. 2015 Sep 16;20(9):16892-907. doi: 10.3390/molecules200916892.
2-Silicon-substituted 1,3-dienes containing non transferrable groups known to promote transmetallation were prepared by Grignard chemistry and enyne metathesis. These dienes participated in one pot metathesis/Diels-Alder reactions in regio- and diastereoselective fashions. Electron-rich alkenes showed the fastest rates in metathesis reactions, and ethylene, a commonly used metathesis promoter slowed enyne metathesis. 2-Pyridyldimethylsilyl and 2-thienyldimethylsilyl substituted Diels-Alder cycloadducts participated in cross-coupling chemistry and the 2-thienyldimethylsilyl substituted cycloadducts underwent cross-coupling under very mild reaction conditions.
通过格氏化学和烯炔复分解反应制备了含有已知可促进金属转移的非可转移基团的2-硅取代的1,3-二烯。这些二烯以区域和非对映选择性方式参与一锅法复分解/狄尔斯-阿尔德反应。富电子烯烃在复分解反应中显示出最快的反应速率，而常用的复分解促进剂乙烯会减缓烯炔复分解反应。2-吡啶基二甲基甲硅烷基和2-噻吩基二甲基甲硅烷基取代的狄尔斯-阿尔德环加成物参与交叉偶联化学，并且2-噻吩基二甲基甲硅烷基取代的环加成物在非常温和的反应条件下进行交叉偶联。
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