Chinese Journal of Organic Chemistry >
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).
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
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
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