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Memory of chirality in the phthalimide photocyclization of adamantane dipeptides

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


Book ID
124113093
Publisher
Elsevier Science
Year
2014
Tongue
French
Weight
412 KB
Volume
55
Category
Article
ISSN
0040-4039

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Memory effect of chirality in the photoc
✍ Stefan Sauer; Andreas Schumacher; Frédérique Barbosa; Bernd Giese 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 209 KB

Photocyclizations of dipeptides 5 and 8 occur mainly with retention of configuration at the stereogenic center of alanine. This memory effect of chirality is explained by a hindered rotation in the two intermediate biradicals 9 and 10 that slows down the equilibration of the radicals.