Facile lewis acid catalyzed synthesis of C(4) symmetric resorcinarenes

MJ McIldowie; M Mocerino; BW Skelton; AH White

doi:10.1021/ol006608u

Facile lewis acid catalyzed synthesis of C(4) symmetric resorcinarenes

Org Lett. 2000 Nov 30;2(24):3869-71. doi: 10.1021/ol006608u.

Authors

MJ McIldowie¹, M Mocerino, BW Skelton, AH White

Affiliation

¹ School of Applied Chemistry, Curtin University of Technology, GPO Box U 1987, Perth, WA 6845, Australia, and Department of Chemistry, University of Western Australia, Nedlands, WA 6907, Australia.

PMID: 11101440
DOI: 10.1021/ol006608u

Abstract

The Lewis acid catalyzed condensation of 3-methoxyphenol with octanal produced the C(4) symmetric calix[4]resorcinarene 2, in high yield. Of the numerous stereo- and regioisomers possible, the rccc isomer with C(4) symmetry was the only product isolated (as a racemate). The structure has been established by single-crystal X-ray structure analysis.