有機催化連鎖1,6/1,4/1,2/1,2-加成反應生成多取代之三環化合物

Abstract

藉由三個分子化合物，進行有機連鎖四階反應，發展高非鏡像選擇性官能基的直並連三環化合物。使用1,3-茚二酮雙烯化合物與乙醯乙酸乙酯，利用20 mol%的硫尿素衍生之有機催化劑及加入20 mol%的1,4-二氮雜二環[2.2.2]辛烷，進行1,6/1,4/1,2/1,2-連鎖反應，得到密集官能基的三環化合物，有優異的產率（高達94%）及非鏡像選擇性（高達>20:1 dr）。此外，也經由單晶繞射X-ray確認其產物相對立體組態；然而，關於鏡像選擇性之有機連鎖反應仍在進行當中。An efficient three components organocascade quadruple reaction has been developed and successfully accessed to the highly diastereoselective functionalized tricyclic compounds. The reaction between arylallylidene-indane-1,3diones and ethyl acetoacetate mediated by thiourea derived organocatalyst and DABCO via 1,6-/1,4-/1,2-/1,2-addition sequence to generate densely functionalized tricyclic outcomes with good yields (up to 94%) and excellent diastereoselectivities (up to >20:1 dr). The relatived configuration of the cyclized product was determined by the single crystal X-ray analysis. However, the enantiomeric version of the organocascade reaction is currently under investigation in our laboratory.