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Stereoselective 1,3-dipolar cycloaddition of a nitrile ylide photochemically generated from 2,3-diphenyl-2H-azirine to substituted methylene lactones
Autoři | |
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Rok publikování | 2000 |
Druh | Článek v odborném periodiku |
Časopis / Zdroj | Collection of Czechoslovak Chemical Communications |
Fakulta / Pracoviště MU | |
Citace | |
www | http://cccc.uochb.cas.cz/ |
Obor | Organická chemie |
Klíčová slova | methylene lactones; nitrile ylide; dipolar cycloaddition; spiro compounds; regioselectivity; stereoselectivity |
Popis | The nitrile ylide photochemically generated from 2,3-diphenyl-2H-azirine adds to both isomers of 3-(tosyloxymethylene)tetrahydrofuran-2-one with excellent regio- and stereoselectivity giving spiroheterocyclic products in moderate yields. X-Ray structure determination showed dibutolactone to have the E-configuration. The corresponding Z-isomer was prepared photochemically. |
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