N,3,4-Trisubstituted pyrrolidines by electron transfer-induced oxidative cyclizations of N-allylic beta-amino ester enolates

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F09%3A00332983" target="_blank" >RIV/61388963:_____/09:00332983 - 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

N,3,4-Trisubstituted pyrrolidines by electron transfer-induced oxidative cyclizations of N-allylic beta-amino ester enolates

Original language description

Oxidative radical cyclizations starting from easily accessible N-allylic beta-alanine esters are reported. Deprotonation generates the corresponding enolates, which are transformed efficiently into alpha-ester radicals by single electron transfer mediated by ferrocenium hexafluorophosphate. The stereochemistry of the radical 5-exo cyclization can be switched by the configuration of the enolate precursor. First examples of asymmetric oxidative radical cyclizations using N-(1-phenylethyl)-substituted beta-amino esters are reported. Only two of the four possible diastereomers are formed from the (E)-enolate with high cis-selectivity. From (Z)-enolates, an additional diastereomer is formed, which is likely to be formed only under chelation control.

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

2009

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

65

Issue of the periodical within the volume

52

Country of publishing house

GB - UNITED KINGDOM

Number of pages

13

Pages from-to

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UT code for WoS article

000272918300021

EID of the result in the Scopus database

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