Flavin-Mediated Visible-Light [2+2] Photocycloaddition of Nitrogen- and Sulfur-Containing Dienes

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F17%3A43914935" target="_blank" >RIV/60461373:22310/17:43914935 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22810/17:43914935
Result on the web
<a href="http://dx.doi.org/10.1002/ejoc.201601377" target="_blank" >http://dx.doi.org/10.1002/ejoc.201601377</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201601377" target="_blank" >10.1002/ejoc.201601377</a>

Result language
angličtina
Original language name
Flavin-Mediated Visible-Light [2+2] Photocycloaddition of Nitrogen- and Sulfur-Containing Dienes
Original language description
The [2+2] photocycloaddition mediated by 1-butyl-3-methyl-7,8-dimethoxyalloxazine (1) has been found to be an effective tool for cyclising omega-phenyl- and omega,omega'-diphenyl-4-aza-1,6-heptadienes, in which the nitrogen atom is protected by acylation or quaternisation, towards the synthesis of a variety of phenyl- and diphenyl-3-azabicyclo[3.2.0]heptanes and their corresponding quaternary salts. Thia derivatives, with the sulfur atom in the form of a sulfone group, underwent an analogous cyclisation. Advantageously, visible light (400 nm) was used for the cycloadditions in the presence of 1, in contrast to the previously described procedures affording azabicyclo[3.2.0]heptanes by using UV irradiation. Practical applications are demonstrated through the synthesis of bicyclic quaternary ammonium salts, 6-phenyl-azabicyclo[3.2.0]heptanesknown to exhibit biological activity or chiral spiro ammonium salts. Flavin 1 was also found to promote the efficient E -> Z isomerisation of electron-rich cinnamyl derivatives to produce mixtures enriched with the Z isomer (with Z/E ratios of up to 77:23).
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry

Project
<a href="/en/project/GA14-09190S" target="_blank" >GA14-09190S: Towards photoorganocatalytic metathesis: [2+2] cycloaddition of alkenes and cyclobutane ring cleavage mediated by flavins and visible light</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2017
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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