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Abstract
An operationally simple E → Z isomerization of activated dienes, based on the β-ionyl motif intrinsic to retinal, is reported using inexpensive (−)-riboflavin (vitamin B2) 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.
Original language | English |
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Pages (from-to) | 9677-9680 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 21 |
Issue number | 23 |
Early online date | 20 Nov 2019 |
DOIs | |
Publication status | Published - 6 Dec 2019 |
Keywords
- retinal isomerization
- molecular editing
- regioselective isomerization
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Dive into the research topics of 'Photocatalytic E→Z Isomerization of β-Ionyl Derivatives'. Together they form a unique fingerprint.Projects
- 1 Finished
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Industrial Case Account 2016 | Livingstone, Keith
Jamieson, C., Tomkinson, N. & Livingstone, K.
EPSRC (Engineering and Physical Sciences Research Council)
1/10/16 → 26/08/20
Project: Research Studentship Case - Internally allocated