在本論文中,我們發展出一種簡單快速之兩步驟合成策略,合成具取代之1-乙烯基茚類化合物(1-vinylindanes)。在此兩步驟合成過程中,第一步驟是利用硼氫化鈉(NaBH4)將具取代的鄰位肉桂基查爾酮(ο-cinnamyl chalcones)進行還原反應,第二步驟再透過三氟化硼(BF3•OEt2),進行分子內環化反應,來獲得乙烯基烯醇茚類化合物。我們使用肉桂烯酮(cinnamyl-enone)為起始物進行分子內環化反應,來獲得高產率之乙烯基烯醇茚類產物,並藉由分子內環化反應來建構出具反式-反式(trans-trans)三個連續性不對稱中心之立體位向,以及具一個(E)-構型的烯類(alkenyl)或苯乙烯(styryl)取代之茚類化合物。並推導出可能機制及使用X-ray單晶繞射儀驗證產物之結構。
This study develops a concise route for the synthesis of 1-vinyl indanes is described, including (1) NaBH4-mediated reduction of ο-cinnamyl chalcones and (2) sequential BF3•OEt2-mediated intramolecular annulation of resulting alkenols. This protocol provides highly effective stereocontrolled cinnamyl-enone cross-coupling to construct three contiguous trans-trans sterecenters and one (E)-configured alkenyl or styryl group. plausible mechanism is proposed and the final product structure confirmed by Single-Crystal X-Ray Diffractometer.