Stereoselective 1,3-dipolar cycloaddition of a nitrile ylide photochemically generated from 2,3-diphenyl-2H-azirine to substituted methylene lactones

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Authors	ČASTULÍK Jakub JONAS Jaroslav MAZAL Ctibor
Year of publication	2000
Type	Article in Periodical
Magazine / Source	Collection of Czechoslovak Chemical Communications
MU Faculty or unit	Faculty of Science
Citation
Web	http://cccc.uochb.cas.cz/
Field	Organic chemistry
Keywords	methylene lactones; nitrile ylide; dipolar cycloaddition; spiro compounds; regioselectivity; stereoselectivity
Description	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.
Related projects:	Structure and character of bonding, properties and analysis of synthetic and natural molecular ensembles