Photochemical Uncaging of Aldehydes and Ketones via Photocyclization/Fragmentation Cascades of Enyne Alcohols: An Unusual Application for a Cycloaromatization Process
- Resource Type
- article
- Authors
- Adam Campbell; Nikolas R. Dos Santos; Igor Alabugin
- Source
- Molecules, Vol 28, Iss 15, p 5704 (2023)
- Subject
- photoremovable protecting groups
photouncaging
cycloaromatization
aldehyde synthesis
ketone synthesis
Organic chemistry
QD241-441
- Language
- English
- ISSN
- 1420-3049
We utilized a cycloaromatization reaction driven by relief of excited state antiaromaticity to photouncage aldehydes and ketones. We developed several synthetic routes towards the synthesis of photocaged carbonyls as allylically substituted 3-(2-(arylethynyl)phenyl)prop-2-en-1-ols. A library of photocaged aryl aldehydes and ketones containing donors and acceptors, as well as several photocaged fragrance aldehydes and the steroid 5α-cholestan- 3 -one, were synthesized and demonstrated photouncaging in good to excellent yields.