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.
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