Synthesis of cyclopropyl silyl ethers and their facile ring opening by photoinduced electron transfer as key step in radical/radical cationic cascade reactions

Various ring-fused cyclopropyl silyl ethers with an benzylic, olefinic or acetylenic side chain have been synthesized. Upon oxidative photoinduced electron transfer (PET) the cyclopropane ring opens and forms a reactive β-keto radical, which undergoes intramolecular cyclization. In some cases we obs...

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Bibliographic Details
Published in:Tetrahedron 2005-10, Vol.61 (43), p.10321-10330
Main Authors: Waske, Prashant A., Mattay, Jochen
Format: Article
Language:English
Subjects:
Domino reactions
Electron transfer
Polycycles
Radical ions
Radical reactions
Siloxy cyclopropanes
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Summary:Various ring-fused cyclopropyl silyl ethers with an benzylic, olefinic or acetylenic side chain have been synthesized. Upon oxidative photoinduced electron transfer (PET) the cyclopropane ring opens and forms a reactive β-keto radical, which undergoes intramolecular cyclization. In some cases we observed only formation of ring opened non-cyclized products. With olefinic side chain 5- exo- trig mode of cyclization rather than 6- endo- trig mode of cyclization takes place whereas in case of acetylenic side chain we observed 6- endo cyclization. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.08.034