Naslov
Memory of chirality in photocyclization of alanine derivatives of adamantylphthalimide

Autori
Spahić, Zlatan ; Sohora, Margareta ; Basarić, Nikola ; Mlinarić-Majerski, Kata

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
24. Hrvatski skup kemičara i kemijskih inženjera (HSKIKI) . knjiga sažetaka / - Zagreb, 2015, Xx-xx

Skup
Hrvatski skup kemičara i kemijskih inženjera (24 ; 2015)

Mjesto i datum
Zagreb, Hrvatska, 21.04.2015. - 24.04.2015

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
photochemistry ; phthalimides ; chirality

Sažetak
Within the scope of investigation of photochemical reactivity of different adamantane derivatives activated by phthalimide chromophore [1] we turned our attention to the photodecarboxylative cyclizations of oligopeptides [2], and discovered that photocyclization of phenylalanine dipeptide 1 proceeds in good yields (65%) and very high enantioselectivity (ee>99%) to macrocyclic product 2. The result was explained by memory of chirality [3]. To test the scope of the enantioselective photocyclization, new dipeptide analogues have to be prepared and the enantioselectivity in the photocyclization reaction investigated. In particular, the emphasis is given to determine the influence of the amino acid residue of dipeptide on the memory of chirality. Herein we report the synthesis and structural characterization of two new alanine dipeptides 3a and 3b, and investigation of their photochemical reactivity.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA