Stereoselective Reactions of (E,E)-2,3,6,7-Tetramethyl-1,8-Bis(trimethylsilyl)octa-2,6-diene with Aldehydes and Acyl Chlorides
作者:Chahinez Aouf、Douniazad El Abed、Malika Ibrahim-Ouali、Michel Giorgi、Maurice Santelli
DOI:10.1002/ejoc.200700137
日期:2007.7
The titanium tetrachloride mediated addition reaction of (E,E)-2,3,6,7-tetramethyl-1,8-bis(trimethylsilyl)octa-2,6-diene to aldehydes and acyl chlorides is described. Aldehydes undergo simple allylation except p-anisaldehyde, which leads to cyclopentane resulting from double allylation. From acyl chlorides, highly substituted meso cyclopentanols bearing 1,3-diquaternary carbon atoms separated by a
描述了四氯化钛介导的 (E,E)-2,3,6,7-四甲基-1,8-双(三甲基甲硅烷基)八-2,6-二烯与醛和酰氯的加成反应。除对茴香醛外,醛会发生简单的烯丙基化,这会导致双烯丙基化产生环戊烷。从酰氯得到高度取代的内消旋环戊醇,其带有被叔甲醇隔开的 1,3-二季碳原子。X 射线分析证实了两种环戊醇的结构。根据环戊醇的结构,可以提出二烯丙基硅烷对酰氯进行双烯丙基化的反应机理。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)