Potter Robert G, Hughes Thomas S
Department of Chemistry, Cook Physical Sciences Building, University of Vermont, Burlington, VT 05401, USA.
Org Lett. 2007 Mar 29;9(7):1187-90. doi: 10.1021/ol0629770. Epub 2007 Feb 27.
[structure: see text]. Asymmetric carbonylative couplings of benzyl halides have been shown to give heterosubstituted 1,3-diarylacetones in moderate to high yields. These asymmetric ketones were converted via Knoevenagel condensations to tetraarylcyclopentadienones, and further conversion via dehydro-Diels-Alder cycloadditions gave highly heterofunctionalized hexaarylbenzenes with uniquely functionalized aryl groups at the para positions of the central benzene. This method allows control of the substituents on each of four unique pendent aryl group positions, giving rise to substitution patterns not available using symmetrical 1,3-diarylacetones.
[结构：见正文]。已表明苄基卤化物的不对称羰基化偶联反应能以中等至高产率得到杂取代的1,3 - 二芳基丙酮。这些不对称酮通过克诺文纳格尔缩合反应转化为四芳基环戊二烯酮，再通过脱氢 - 狄尔斯 - 阿尔德环加成进一步转化，得到高度杂功能化的六芳基苯，其中心苯的对位带有独特功能化的芳基。该方法能够控制四个独特侧链芳基位置上每个位置的取代基，从而产生使用对称1,3 - 二芳基丙酮无法获得的取代模式。
