陳焜銘Chen, Kwunmin張富傑Chang, Fu-Jie2019-09-04不公開2019-09-042016http://etds.lib.ntnu.edu.tw/cgi-bin/gs32/gsweb.cgi?o=dstdcdr&s=id=%22G060342040S%22.&%22.id.&http://rportal.lib.ntnu.edu.tw:80/handle/20.500.12235/100050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.有機連鎖反應16-加成反應三環Organocascade16-additiontricyclic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Diastereoselective Synthesis of Functionalized Angularly Fused Tricycles via an Organocascade Quadruple Reaction Involving Vinylogous 1,6/1,4/1,2/1,2-Addition Sequence