Synthesis of all stereoisomers of sulfinylcalix[4]arenes

Naoya Morohashi, Hiroshi Katagiri, Nobuhiko Iki, Yusuke Yamane, Chizuko Kabuto, Tetsutaro Hattori, Sotaro Miyano

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37 Citations (Scopus)

Abstract

All four stereoisomers of p-tert-butylsulfinylcalix[4]arene [4(rccc), 4(rcct), 4(rctt), and 4(rtct)], arising from the disposition of the four sulfinyl groups with respect to the mean plane of the four bridging sulfur atoms, have been prepared via oxidation of p-tert-butylthiacalix[4]arene (2) or its tetra-O-benzyl ethers 5 of defined conformations. Thus, treatment of 2 with 4.4 molar equiv of NaBO3· 4H2O gave the rtct and rctt isomers in 27% and 17% yields, respectively, while oxidation of cone 5 (5C) and partial cone 5 (5PC) proceeded stereoselectively to give, after debenzylation of the resulting tetrasulfoxides 12 and 15, the rccc and rcct isomers in 56% and 28% yields, respectively, based on 5. The sulfinylcalix[4]arenes 4 were treated with iodomethane in the presence of a base to give the corresponding tetramethyl ethers 16, the structures of which in regard to the disposition of the sulfinyl groups and the conformation of the phenol units were determined by X-ray crystallography. Also reported is the synthesis of all four conformational isomers of tetra-O-benzyl ether of 2 (5C, 5PC, 51,2-A, and 51,3-A).

Original languageEnglish
Pages (from-to)2324-2333
Number of pages10
JournalJournal of Organic Chemistry
Volume68
Issue number6
DOIs
Publication statusPublished - 2003 Mar 21

ASJC Scopus subject areas

  • Organic Chemistry

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