Novel chiral (salen)Mn(iii) complexes containing a calix[4]arene unit in 1,3-alternate conformation as catalysts for enantioselective epoxidation reactions of (Z)-aryl alkenes

Carmela Bonaccorso, Giovanna Brancatelli, Francesco P. Ballistreri, Silvano Geremia, Andrea Pappalardo, Gaetano A. Tomaselli, Rosa M. Toscano, Domenico Sciotto

Research output: Contribution to journalArticle

Abstract

Two new chiral calix[4]arene-salen ligands 1a,b, based on calix[4]arene platforms in 1,3-alternate conformation, have been prepared by a new general synthetic pathway. Their Mn(iii) complexes, 3a,b, have shown fairly good efficiency in the asymmetric epoxidation of styrene and substituted styrenes, whereas excellent catalytic activity and selectivity were observed with rigid bicyclic alkenes, namely 1,2-dihydro-naphthalene and substituted 2,2′-dimethyl-chromene. The higher catalytic properties of 3a may be ascribed to the more rigid and inherently chiral structure as proved by molecular modelling, NMR spectroscopy and X-ray data of the similarly structured UO2 complexes 2a,b.

Original languageEnglish
Pages (from-to)2183-2193
Number of pages11
JournalDalton Transactions
Volume43
Issue number5
DOIs
Publication statusPublished - Feb 7 2014

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Epoxidation
Alkenes
Conformations
Styrenes
Benzopyrans
Catalysts
Styrene
Molecular modeling
Catalyst selectivity
Nuclear magnetic resonance spectroscopy
Catalyst activity
Ligands
X rays
calix(4)arene
Mn-salen
disalicylaldehyde ethylenediamine
naphthalene

ASJC Scopus subject areas

  • Inorganic Chemistry

Cite this

Novel chiral (salen)Mn(iii) complexes containing a calix[4]arene unit in 1,3-alternate conformation as catalysts for enantioselective epoxidation reactions of (Z)-aryl alkenes. / Bonaccorso, Carmela; Brancatelli, Giovanna; Ballistreri, Francesco P.; Geremia, Silvano; Pappalardo, Andrea; Tomaselli, Gaetano A.; Toscano, Rosa M.; Sciotto, Domenico.

In: Dalton Transactions, Vol. 43, No. 5, 07.02.2014, p. 2183-2193.

Research output: Contribution to journalArticle

Bonaccorso, Carmela ; Brancatelli, Giovanna ; Ballistreri, Francesco P. ; Geremia, Silvano ; Pappalardo, Andrea ; Tomaselli, Gaetano A. ; Toscano, Rosa M. ; Sciotto, Domenico. / Novel chiral (salen)Mn(iii) complexes containing a calix[4]arene unit in 1,3-alternate conformation as catalysts for enantioselective epoxidation reactions of (Z)-aryl alkenes. In: Dalton Transactions. 2014 ; Vol. 43, No. 5. pp. 2183-2193.
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