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Pregled bibliografske jedinice broj: 700334

Časopis

Autori: Šumanovac Ramljak, Tatjana; Sohora, Margareta; Antol, Ivana; Kontrec, Darko; Basarić, Nikola; Mlinarić-Majerski, Kata
Naslov: Memory of chirality in the phthalimide photocyclization of adamantane dipeptides
Izvornik: Tetrahedron letters (0040-4039) 55 (2014), 30; 4078-4081
Vrsta rada: članak
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.
Projekt / tema: 02.05/25, 098-0982904-2910, 098-0982933-2911
Izvorni jezik: ENG
Rad je indeksiran u
bazama podataka:
Current Contents Connect (CCC)
Scopus
SCI-EXP, SSCI i/ili A&HCI
Science Citation Index Expanded (SCI-EXP) (sastavni dio Web of Science Core Collectiona)
Kategorija: Znanstveni
Znanstvena područja:
Kemija
URL Internet adrese: http://www.sciencedirect.com/science/article/pii/S0040403914009514
Broj citata:
Altmetric:
DOI: 10.1016/j.tetlet.2014.05.118
URL cjelovitog teksta:
Google Scholar: Memory of chirality in the phthalimide photocyclization of adamantane dipeptides
Upisao u CROSBI: Enidija Lukša (Enidija.Luksa@irb.hr), 6. Lip. 2014. u 09:51 sati



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