Stereoselective preparation of (Z)-2-(trialkylsilyloxy)-2-alkenals by retrocycloaddition reactions of 4H-4-alkyl-5-(trialkylsilyloxy)-1,3-dioxins.: Useful reactants for Lewis acid catalyzed [4+3] cyclizations
Stereoselective preparation of (Z)-2-(trialkylsilyloxy)-2-alkenals by retrocycloaddition reactions of 4H-4-alkyl-5-(trialkylsilyloxy)-1,3-dioxins.: Useful reactants for Lewis acid catalyzed [4+3] cyclizations
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DOI：
10.1021/ol016668f
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发表时间：
2001-11-01
期刊：
影响因子：
5.2
通讯作者：
Funk, RL
中科院分区：
文献类型：
--
作者：
Aungst, RA;Funk, RL
[图示]4H-4-烷基-5-(三烷基甲硅烷氧基)-1,3-二恶英的逆环加成在回流甲苯中顺利进行，得到具有完全立体选择性的(Z)-2-(三烷基甲硅烷氧基)-2-烯醛。这些烯醛在路易斯酸存在下与二烯进行佐佐木型[4 + 3]环化，在许多情况下具有优异的区域选择性和/或立体选择性。
[GRAPHICS]Retrocycloadditions of 4H-4-alkyl-5-(trialylsilyloxy)-1,3-dioxins proceed smoothly in refluxing toluene to afford (Z)-2-(trialkylsilyloxy)-2-alkenals with complete stereos electivity. These enals undergo Sasaki-type [4 + 3] cyclizations with dienes in the presence of Lewis acids, in many instances with excellent regio- and/or stereoselectivity.