A net anti-selective dialkylation of the proximal hydroxy groups of thiacalixarene 2 is achieved for the first time via the initial protection of the two proximal hydroxy groups of compound 2 with Tf moieties by intramolecular rearrangement of easily preparable 1,3-bistriflate ester 3 to 1,2-counterpart 4, followed by anti-selective dialkylation of the remaining hydroxy groups with alkyl halides or under the Mitsunobu conditions and subsequent removal of the Tf moieties.
- Intramolecular ester exchange
- anti-Selective 1,2-dialkylation
ASJC Scopus subject areas
- Drug Discovery
- Organic Chemistry