期刊
ORGANIC LETTERS
卷 21, 期 23, 页码 9677-9680出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b03842
关键词
-
资金
- WWU Munster
- Royal Society of Chemistry [RM1802-6141]
- Deutsche Forschungsgemeinschaft (DFG Return Fellowship)
An operationally simple E -> Z isomerization of activated dienes, based on the beta-ionyl motif intrinsic to retinal, is reported using inexpensive (-)-riboflavin (vitamin B-2) under irradiation at 402 nm. Selective energy transfer from photoexcited (-)-riboflavin to the starting E-isomer enables geometrical isomerization. Since the analogous process with the Z-isomer is inefficient, microscopic reversibility is circumvented, thereby enabling a directional isomerization to generate the contra-thermodynamic product (up to 99% yield, up to 99:1 Z/E). Prudent choice of photocatalyst enables chemoselective isomerization to be achieved in both inter- and intramolecular systems. The principles established from this study, together with a molecular editing approach, have facilitated the development of a regioselective isomerization of a truncated triene based on the retinal scaffold.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据