Optically active calixarenes conduced by methylene substitution

Journal of the American Chemical Society
Vijay GopalsamuthiramWilliam D Wulff

Abstract

The first method for the synthesis of optically active calix[4]arenes that are chiral as a result of substitution on the methylene bridges is described. The key step in the synthesis involves the reaction of a biscarbene complex with a diyne, which generates two of the benzene rings and the macrocyclic ring of the calix in a single transformation. The utility of this triple annulation process is demonstrated in the synthesis of di- and tetramethoxycalix[4]arenes. The flexibility of this synthetic approach is demonstrated by the synthesis of two diastereomers of the tetramethoxycalix[4]arenes in which each is synthesized in a stereoselective fashion by proper control of the absolute configurations of the methoxy groups in the biscarbene complex and in the diyne.

References

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Apr 26, 2003·The Journal of Organic Chemistry·Samah Simaan, Silvio E Biali
Oct 28, 2004·Journal of the American Chemical Society·Vijay Gopalsamuthiram, William D Wulff
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Citations

May 4, 2011·Journal of the American Chemical Society·Gretchen R StantonPatrick J Walsh
Apr 13, 2011·The Journal of Organic Chemistry·Lev Kuno, Silvio E Biali
Aug 11, 2011·The Journal of Organic Chemistry·Katerina Kogan, Silvio E Biali
Dec 25, 2013·The Journal of Organic Chemistry·David PomsSilvio E Biali
Oct 12, 2010·Chemical Communications : Chem Comm·Vijay GopalsamuthiramWilliam D Wulff
Aug 12, 2014·European Journal of Medicinal Chemistry·Meng Li, Bao-Xiang Zhao
May 24, 2019·Chemistry : a European Journal·Ori Shalev, Silvio E Biali
Nov 28, 2012·Angewandte Chemie·Alexander V PredeusWilliam D Wulff
Apr 28, 2010·The Journal of Organic Chemistry·Norbert Itzhak, Silvio E Biali
Oct 12, 2017·Organic Letters·Illan KimSanghee Kim
Aug 30, 2014·The Journal of Organic Chemistry·Ori Shalev, Silvio E Biali
May 24, 2018·Organic Letters·Ori Shalev, Silvio E Biali

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