Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (3): 646-651.DOI: 10.6023/cjoc201609014 Previous Articles     Next Articles

ARTICLE

原位制备联烯酯的分子间[2+2]环加成反应研究

赵立芳, 同晓娟, 祝海涛, 杨得锁, 凡明锦   

  1. 宝鸡文理学院化学化工学院 宝鸡 721013
  • 收稿日期:2016-09-13 修回日期:2016-11-01 出版日期:2017-03-25 发布日期:2016-12-02
  • 通讯作者: 祝海涛,E-mail:zhuht@bjwlxy.edu.cn E-mail:zhuht@bjwlxy.edu.cn
  • 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

Zhao Lifang, Tong Xiaojuan, Zhu Haitao, Yang Desuo, Fan Mingjin   

  1. College of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji 721013
  • Received:2016-09-13 Revised:2016-11-01 Online:2017-03-25 Published:2016-12-02
  • Contact: 10.6023/cjoc201609014 E-mail:zhuht@bjwlxy.edu.cn
  • 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).

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