Diazadioxadecalin and salen podands and macrocycles within dynamic combinatorial virtual libraries: Structure, prototropy, complexation and enantioselective catalysis

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Abstract

The reactions of L-1,4-diaminobutanediol (3) and D-2,3-diaminobutanediol (4) with salicyl aldehyde provide the tautomeric manifolds of L-1,4-bis(salicylideneamino)-2,3-butanediol (5) and D-2,3-bis(salicylideneamino)-1,4-butanediol (6), respectively. O-alkylation of the salicyl moiety stabilizes the closed dioxadiazadecalin (DODAD) and diazadioxadecalin (DADOD) isomers (7″, 8″) and accordingly, the dialdehyde 1,2-bis(o-formylphenoxy)-ethane (9) led to the respective macrocyclic manifolds (10-10″ and 11-11″). These tautomeric manifolds are typical target-driven dynamic combinatorial virtual libraries, which can be biased by complex formation with metal ions of different ionic radius. A rare instance of simultaneous occurrence of keto-enamine and phenol-imine tautomers in the solid state of 6 was unravelled (X-ray at two temperatures) and the strength of the intramolecular hydrogen bonding (and hence, the extent of ring closure) in 6 is temperature dependent. Compounds 6, 11 and 12-14 constitute a new class of salens, which form heavy and transition metal complexes. Some such Mn(III) complexes are good chirality inducing catalysts, as found in asymmetric indene epoxidation reactions.

Original languageEnglish
Pages (from-to)67-77
Number of pages11
JournalJournal of Organometallic Chemistry
Volume630
Issue number1
DOIs
StatePublished - 2 Jul 2001

Keywords

  • Combinatorial virtual libraries
  • Complexes
  • Dioxadiazadecalins
  • Enantioselective catalysis
  • Salens
  • Tautomerism

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