Memory of chirality in the phthalimide photocyclization of adamantane dipeptides

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

doi:10.1016/j.tetlet.2014.05.118

Pregled bibliografske jedinice broj: 700334

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)

CROSBI ID: 700334 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

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

Projekti:
098-0982933-2911 - Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima (Majerski, Kata, MZOS ) ( CroRIS)
02.05/25 - Fotokemija policikličkih molekula: od istraživanja mehanizama reakcije do novih lijekova i medicinskih primjena (Basarić, Nikola, HRZZ ) ( CroRIS)
098-0982904-2910 - Kiralni organski materijali – sintetska, strukturna i funkcionalna istraživanja (Vinković, Vladimir, MZOS ) ( CroRIS)

Ustanove:
Institut "Ruđer Bošković", Zagreb

Profili:

Nikola Basarić (autor)