Diastereoselectivity in 1,3-dipolar cycloaddition reactions of alpha-methylene lactone derivatives

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Authors	ČASTULÍK Jakub MELŠA Petr MAZAL Ctibor
Year of publication	2001
Type	Article in Proceedings
Conference	9th Meeting on Stereochemistry, Book of Abstracts
MU Faculty or unit	Faculty of Science
Citation
Field	Organic chemistry
Keywords	Stereoselectivity; Methylene Lactones; 1;3-Dipolar Cycloaddition
Description	Alpha-methylene lactones added stereoselectively various kinds of 1,3-dipolar compounds. Spiro pyrrolidines and spiro pyrrolizidines were prepared by addition of azomethin ylides generated from sarcosin and prolin resp. Cycloaddition of a photochemically generated nitril ylide showed an unusual exo-selectivity. Alpha-methylene-gamma-lactone with a bulky substituent (OBO) in gamma position, which was prepared as a single enantiomer from L-glutamic acid, added 1,3-dipolar compounds in anti-manner almost exclusively.
Related projects:	Structure and character of bonding, properties and analysis of synthetic and natural molecular ensembles