O,O″- and O,O′-bis(2-aminoethyl)-p-tert-butylthiacalixarenes of anti conformation have been prepared by the reduction of the corresponding O,O″- and O,O′-bis(cyanomethyl) ethers. Their syn-O,O″- and O,O′-counterparts have been prepared by alternative routes via the Mitsunobu reaction of thiacalixarene with N-(2-hydroxyethyl)phthalimide and the reduction of a O,O′-disiloxanediyl-bridged O″,O‴- bis(cyanomethyl) ether of 1,2-alternate conformation, respectively. These products are expected to serve as useful precursors of highly elaborated synthetic receptors, including biscalixarenes.
- Stereoselective functionalization
ASJC Scopus subject areas
- Drug Discovery
- Organic Chemistry