原位制备联烯酯的分子间[2+2]环加成反应研究
收稿日期: 2016-09-13
修回日期: 2016-11-01
网络出版日期: 2016-12-02
基金资助
陕西省教育厅重点实验室（Nos.15JS006，14JS005）、宝鸡文理学院博士科研启动计划（Nos.ZK15045，ZK16060）资助项目.
Intermolecular[2+2] Cycloaddition of in-situ Generated Allenylic Esters
Received date: 2016-09-13
Revised date: 2016-11-01
Online published: 2016-12-02
Supported by
Project supported by the Education Department of Shaanxi Province Key Laboratory Project (Nos. 15JS006, 14JS005), and the Ph.D. Scientific Research Projects of Baoji University of Arts and Sciences (Nos. ZK15045, ZK16060).
赵立芳 , 同晓娟 , 祝海涛 , 杨得锁 , 凡明锦 . 原位制备联烯酯的分子间[2+2]环加成反应研究[J]. 有机化学, 2017 , 37(3) : 646 -651 . DOI: 10.6023/cjoc201609014
The development of a convenient and effective[2+2] cycloaddition for the synthesis of highly substituted cyclobutanes with excellent selectivity is of great scientific significance. Using p-toluenesulfonic acid monohydrate (TsOH·H2O) as catalyst and pyridinium chlorochromate (PCC) as oxidant, the intermolecular[2+2] cycloaddition of allenylic esters generated in-situ from 2-(3-hydroxy-3,3-diphenylprop)benzaldehydes to constructure various cyclobutane compounds is reported. This protocol has some distinct advantages of mild reaction conditions, atom economy and high regioselectivity. The structures of relevant products were characterized by 1H NMR, 13C NMR, HRMS and X-ray crystal diffraction. In addition, a possible mechanism for this transformation was depicted.
Key words： allenylic esters; propargyl alcohols; [2+2]-cycloaddition; cyclobutanes
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