通过微波辅助串联氧负离子5-外环化-克莱森重排过程合成七元碳环
Synthesis of seven-membered carbocyclic rings via a microwave-assisted tandem oxyanionic 5-exo dig cyclization-claisen rearrangement process.
作者信息
Li Xin, Kyne Robert E, Ovaska Timo V
机构信息
Department of Chemistry, Connecticut College, 270 Mohegan Avenue, New London, Connecticut 06320, USA.
出版信息
J Org Chem. 2007 Aug 17;72(17):6624-7. doi: 10.1021/jo0710432. Epub 2007 Jul 27.
Abstract
Appropriately substituted 1-alkenyl-4-pentyn-1-ol systems, readily prepared from simple starting materials, serve as useful precursors to a number of substituted cyclohept-4-enone derivatives via a microwave-assisted tandem oxyanionic 5-exo cyclization/Claisen rearrangement sequence. The reactions involving terminally substituted 4-pentyn-1-ols were found to be highly stereoselective, with the alpha and beta groups in the final product showing a strong preference for the trans orientation.
摘要
由简单起始原料易于制备的适当取代的1-烯基-4-戊炔-1-醇体系，通过微波辅助串联氧负离子5-外环化/克莱森重排序列，可作为多种取代的环庚-4-烯酮衍生物的有用前体。发现涉及末端取代的4-戊炔-1-醇的反应具有高度立体选择性，最终产物中的α和β基团强烈倾向于反式取向。
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