Template-Directed Selective Photodimerization Reactions of 5-Arylpenta-2,4-dienoic Acids
JOURNAL OF ORGANIC CHEMISTRY, cilt.89, sa.14, ss.10409-10418, 2024 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 89 Sayı: 14
- Basım Tarihi: 2024
- Doi Numarası: 10.1021/acs.joc.4c01374
- Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC), Current Chemical Reactions (CCR)
- Sayfa Sayıları: ss.10409-10418
- Orta Doğu Teknik Üniversitesi Adresli: Hayır
Özet
We developed an efficient method that enables selective photodimerization of 5-arylpenta-2,4-dienoic acids (i.e., vinylogous cinnamic acids). The use of 1,8-dihydroxynaphthalene as a template ensures proximity of the two reacting olefins so that irradiation of template-bound dienoic acids gives mono [2 + 2] cycloaddition products in good to excellent yields (up to 99%), as single regioisomers, and with high diastereoselectivities (dr = 3:1 to 13:1). The geometrical and stereochemical features of compounds 12a, 16a, and 22a were analyzed by X-ray crystallography.