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

Warning

This publication doesn't include Institute of Computer Science. It includes Faculty of Science. Official publication website can be found on muni.cz.

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