| ČASTULÍK, Jakub, Jaromír MAREK a Ctibor MAZAL. Synthesis of spiropyrrolidines and spiropyrrolizidines by 1,3-dipolar cycloadditions of azomethine ylides to substituted a-methylene-g-lactones. Tetrahedron. Oxford (UK): Elsevier Science Ltd., 2001, roč. 57, č. 39, s. 8339-8347. ISSN 0040-4020. |
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@article{371791,
author = {Častulík, Jakub and Marek, Jaromír and Mazal, Ctibor},
article_location = {Oxford (UK)},
article_number = {39},
keywords = {cycloadditions; methylene lactones; azomethine ylides; regioselectivity; stereoselectivity},
language = {eng},
issn = {0040-4020},
journal = {Tetrahedron},
title = {Synthesis of spiropyrrolidines and spiropyrrolizidines by 1,3-dipolar cycloadditions of azomethine ylides to substituted a-methylene-g-lactones},
volume = {57},
year = {2001}
}
TY - JOUR
ID - 371791
AU - Častulík, Jakub - Marek, Jaromír - Mazal, Ctibor
PY - 2001
TI - Synthesis of spiropyrrolidines and spiropyrrolizidines by 1,3-dipolar cycloadditions of azomethine ylides to substituted a-methylene-g-lactones
JF - Tetrahedron
VL - 57
IS - 39
SP - 8339
EP - 8339
PB - Elsevier Science Ltd.
SN - 00404020
KW - cycloadditions
KW - methylene lactones
KW - azomethine ylides
KW - regioselectivity
KW - stereoselectivity
N2 - 1,3-Dipolar cycloadditions of (E)- and (Z)-substituted alpha -methylene-gamma -lactones with azomethine ylides derived from N-methyl glycine and L-proline gave the corresponding spiropyrrolidine and spiropyrrolizidine cycloadducts in good to moderate yields with various extent of stereoselectivity and regioselectivity. Cycloadditions of the azomethine ylide derived from L-proline exhibited endo selectivity especially in the case of (Z)-isomers of starting methylene lactones. Reactivity and regioselectivity were rationalized by a comparison with quantum chemical calculations (AM1). Structures of derivatives prepared were determined by NMR spectroscopy and by X-ray.
ER -
ČASTULÍK, Jakub, Jaromír MAREK a Ctibor MAZAL. Synthesis of spiropyrrolidines and spiropyrrolizidines by 1,3-dipolar cycloadditions of azomethine ylides to substituted a-methylene-g-lactones. \textit{Tetrahedron}. Oxford (UK): Elsevier Science Ltd., 2001, roč.~57, č.~39, s.~8339-8347. ISSN~0040-4020.
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