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Memory of chirality in the phthalimide photocyclization of adamantane dipeptides


Šumanovac Ramljak, Tatjana; Sohora, Margareta; Antol, Ivana; Kontrec, Darko; Basarić, Nikola; Mlinarić-Majerski, Kata
Memory of chirality in the phthalimide photocyclization of adamantane dipeptides // Tetrahedron letters, 55 (2014), 30; 4078-4081 doi:10.1016/j.tetlet.2014.05.118 (međunarodna recenzija, članak, znanstveni)


Naslov
Memory of chirality in the phthalimide photocyclization of adamantane dipeptides

Autori
Šumanovac Ramljak, Tatjana ; Sohora, Margareta ; Antol, Ivana ; Kontrec, Darko ; Basarić, Nikola ; Mlinarić-Majerski, Kata

Izvornik
Tetrahedron letters (0040-4039) 55 (2014), 30; 4078-4081

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

Ključne riječi
Diazaheterocycles ; Dipeptides ; Enantioselective cyclization ; Photochemistry ; Photodecarboxylation ; Phthalimides

Sažetak
Upon sensitized irradiation of N-phthalimido dipeptides continaing L- or D-phenylalanine, enantioselective cyclization to diazamacrocycles takes place (ee >99%). The high optical purity of the products was explained by the memory of chirality effect. The chirality is preserved owing to the axial chirality of the biradical intermediate formed. An insight into the origin behind the enantioselective cyclization of the intermediate was given by density functional calculations. The very high enantiomeric excess in this type of photocyclization establishes it as a new method for the enantioselective synthesis of different large aza-heterocycles.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
02.05/25
098-0982904-2910 - Kiralni organski materijali – sintetska, strukturna i funkcionalna istraživanja (Vladimir Vinković, )
098-0982933-2911 - Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima (Kata Majerski, )

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


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