Bisallylation of Zirconacyclopentenes and Ring-Closing Metathesis: A Route to Eight-Membered-Ring Compounds
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F16%3A10323636" target="_blank" >RIV/00216208:11310/16:10323636 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1055/s-0035-1560587" target="_blank" >http://dx.doi.org/10.1055/s-0035-1560587</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1055/s-0035-1560587" target="_blank" >10.1055/s-0035-1560587</a>
Alternative languages
Result language
angličtina
Original language name
Bisallylation of Zirconacyclopentenes and Ring-Closing Metathesis: A Route to Eight-Membered-Ring Compounds
Original language description
The cyclization of various enynes with the Negishi reagent provides the corresponding bicyclic zirconacyclopentenes, which after exposure to allyl chloride in the presence of a catalytic amount of copper(I) chloride, undergo bisallylation to furnish 1,9-decadienes in good yields (42-89%). The dienes are subjected to ring-closing metathesis to afford bicyclic compounds with [6.3.0]bicycloundecane (8,5-fused ring system) or [6.4.0]bicyclododecane (8,6-fused ring system) frameworks in good to excellent yields (52-92%). Selective monoallylation of a selected zirconacyclopentene followed by carboxyethylation with ethyl chloroformate gives rise to the corresponding ester, which after metalation and reaction with allyl bromide, furnishes a 1,9-decadiene. Ring-closing metathesis then yields the expected eight-membered cyclic product in 92% yield. This procedure constitutes a new pathway to bicyclic carbocyclic systems starting from 1,-enynes.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
<a href="/en/project/GA13-15915S" target="_blank" >GA13-15915S: Development of zirconocene-based methods for sesquiterpenoids synthesis</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Synlett
ISSN
0936-5214
e-ISSN
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Volume of the periodical
27
Issue of the periodical within the volume
3
Country of publishing house
DE - GERMANY
Number of pages
5
Pages from-to
432-436
UT code for WoS article
000369724300020
EID of the result in the Scopus database
2-s2.0-84956662742