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Pregled bibliografske jedinice broj: 299610

Macrocyclic Bis(oxazoline) Cu(I) Complexes – Structure/Stereoselectivity Relationships in Catalytic Cyclopropanations


Portada, Tomislav; Roje, Marin; Raza, Zlata; Čaplar, Vesna; Žinić, Mladen; Šunjić, Vitomir
Macrocyclic Bis(oxazoline) Cu(I) Complexes – Structure/Stereoselectivity Relationships in Catalytic Cyclopropanations // European Journal of Organic Chemistry, 2007 (2007), 5; 838-856 (međunarodna recenzija, članak, znanstveni)


Naslov
Macrocyclic Bis(oxazoline) Cu(I) Complexes – Structure/Stereoselectivity Relationships in Catalytic Cyclopropanations

Autori
Portada, Tomislav ; Roje, Marin ; Raza, Zlata ; Čaplar, Vesna ; Žinić, Mladen ; Šunjić, Vitomir

Izvornik
European Journal of Organic Chemistry (1434-193X) 2007 (2007), 5; 838-856

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Bis(oxazolines) • catalytic cyclopropanation • copper(I) complexes • diastereoselectivity • macrocyclic ligands

Sažetak
The design and synthesis of 18 chiral macrocycles with built in C2-symmetric bis(oxazoline) units is described and the catalytic properties of their copper(I) complexes in cyclopropanations of styrene with ethyl diazoacetate are assessed. The bridging of two homochiral centers in the bis(oxazoline) unit gives a macrocyclic ligand, which upon binding of Cu(I) is transformed into a macrocyclic catalytic complex containing a chiral cavity. Such a complex represents a conceptually new type of supramolecular organometallic catalyst, possessing a chiral reaction cavity. A clear relationship between catalyst structures and the stereoselectivity outcome in the catalytic cyclopropanations has been established and it is demonstrated that both the enantioselectivity and the diastereoselectivity can be independently modified by variation of the ligand structural parameters. The Cu(I) complex of the ligand 3b gave a trans/cis diastereomeric ratio of 94:6 (de = 88 %), representing the highest diastereoselectivity obtained to date for cyclopropanations catalyzed by the bis(oxazoline) class of complexes. An explanation of the observed relationship between stereochemical outcome and ligand structure is proposed.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
098-0982904-2912 - Samo-udruživanje u gelovima i sinteza funkcionalnih hibridnih materijala (Leo Frkanec, )
098-0982914-2935 - Sinteza novih biološki aktivnih derivata nukleobaza i nukleotida (Biserka Žinić, )
098-0982933-2908 - Kiralni građevni blokovi za biološki aktivne molekule. Sinteza i reaktivnost (Zdenko Hameršak, )

Ustanove
Institut "Ruđer Bošković", Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


Uključenost u ostale bibliografske baze podataka:


  • CA Search (Chemical Abstracts)