Podand ionophores with dialkoxy conformational locks

Ionophores 2–4 which incorporate a novel + gauchel-gauche dialkoxy conformational locking mechanism were synthesized from D-mannitol. These new podands bound various chiral ammonium ions enantioselectively, but comparisons with related alkylated podands indicated that dialkyl and dialkoxy conformati...

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Bibliographic Details
Published inTetrahedron letters Vol. 34; no. 42; pp. 6701 - 6704
Main Authors Tang, Suhan, Still, W.Clark
Format Journal Article
LanguageEnglish
Published Oxford Elsevier Ltd 15.10.1993
Elsevier
Subjects
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
Oxygen sulfur heterocycle
Organic cation
Cyclization
Enantioselectivity
Six membered ring
Ion extraction
Acid catalysis
Polyol
Oxygen heterocycle
Podand
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Summary:Ionophores 2–4 which incorporate a novel + gauchel-gauche dialkoxy conformational locking mechanism were synthesized from D-mannitol. These new podands bound various chiral ammonium ions enantioselectively, but comparisons with related alkylated podands indicated that dialkyl and dialkoxy conformational locks are not completely interchangable. Three new, enantioselective podand ionophores are prepared from D-mannitol and incorporate a conformational locking mechanism which is controlled by the electrostatic interactions of alkoxy groups.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)61679-9