Synthesis of spiropyrrolidines and spiropyrrolizidines by 1,3-dipolar cycloadditions of azomethine ylides to substituted a-methylene-g-lactones

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F01%3A00004532" target="_blank" >RIV/00216224:14310/01:00004532 - isvavai.cz</a>

Result on the web

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DOI - Digital Object Identifier

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Result language

angličtina

Original language name

Synthesis of spiropyrrolidines and spiropyrrolizidines by 1,3-dipolar cycloadditions of azomethine ylides to substituted a-methylene-g-lactones

Original language description

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.

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

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Continuities

Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2001

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Tetrahedron

ISSN

0040-4020

e-ISSN

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Volume of the periodical

57

Issue of the periodical within the volume

39

Country of publishing house

GB - UNITED KINGDOM

Number of pages

9

Pages from-to

8339

UT code for WoS article

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EID of the result in the Scopus database

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