Abstract
A net anti-selective dialkylation of the proximal hydroxy groups of thiacalix[4]arene 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.
Original language | English |
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Pages (from-to) | 6281-6285 |
Number of pages | 5 |
Journal | Tetrahedron Letters |
Volume | 48 |
Issue number | 36 |
DOIs | |
Publication status | Published - 2007 Sep 3 |
Keywords
- Intramolecular ester exchange
- Thiacalix[4]arene
- anti-Selective 1,2-dialkylation
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry