手性双模式、超分子双非对映体选择性光环二聚化 2-蒽羧酸酯与直链淀粉支架键合。
Dual chiral, dual supramolecular diastereodifferentiating photocyclodimerization of 2-anthracenecarboxylate tethered to amylose scaffold.
机构信息
Department of Applied Chemistry, Osaka University, 2-1 Yamada-oka, Suita 565-0871, Japan.
出版信息
Org Lett. 2010 Aug 6;12(15):3510-3. doi: 10.1021/ol101362s.
Newly synthesized 6-O-(2-anthroyl)amylose (AC-Am; 51% substitution) was photolyzed in (aqueous) DMSO solutions to give HH dimers as major products (after saponification), with modest enantiomeric excesses (ee) of 12-15% and 1-2% for syn-HT and anti-HH dimers, respectively. Addition of gamma-cyclodextrin switched the product selectivity to HT and enhanced the ee of syn-HT up to 37%, while the chiral sense of anti-HH was inverted by changing the irradiation temperature, demonstrating usefulness of the dual-supramolecular approach to photochirogenesis.
新合成的 6-O-(2-蒽基)淀粉 (AC-Am; 51%取代) 在 (含水) DMSO 溶液中光解，得到 HH 二聚体作为主要产物(皂化后)，对映体过量值 (ee) 分别为 12-15%和 1-2%，用于 syn-HT 和 anti-HH 二聚体。添加 γ-环糊精将产物选择性切换到 HT，并将 syn-HT 的 ee 提高到 37%，而通过改变照射温度，反式-HH 的手性被反转，证明了双超分子方法在光致手性中的有用性。
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