Citation: Zhao Lifang, Tong Xiaojuan, Zhu Haitao, Yang Desuo, Fan Mingjin. Intermolecular[2+2] Cycloaddition of in-situ Generated Allenylic Esters[J]. Chinese Journal of Organic Chemistry, ;2017, 37(3): 646-651. doi: 10.6023/cjoc201609014 shu

Intermolecular[2+2] Cycloaddition of in-situ Generated Allenylic Esters

College of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji 721013

Corresponding author: Zhu Haitao, zhuht@bjwlxy.edu.cn
Received Date: 13 September 2016
Revised Date: 1 November 2016

Fund Project: the Ph.D. Scientific Research Projects of Baoji University of Arts and Sciences ZK15045the Ph.D. Scientific Research Projects of Baoji University of Arts and Sciences ZK15045Project supported by the Education Department of Shaanxi Province Key Laboratory Project 15JS006Project supported by the Education Department of Shaanxi Province Key Laboratory Project 14JS005

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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.
- allenylic esters,
- propargyl alcohols,
- [2+2]-cycloaddition,
- cyclobutanes
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