Enantioselective Allylation of beta-Haloacrylaldehydes: Formal Total Syntheses of Pteroenone and Antillatoxin

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F16%3A10323774" target="_blank" >RIV/00216208:11310/16:10323774 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1002/ejoc.201600286" target="_blank" >http://dx.doi.org/10.1002/ejoc.201600286</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201600286" target="_blank" >10.1002/ejoc.201600286</a>

Result language
angličtina
Original language name
Enantioselective Allylation of beta-Haloacrylaldehydes: Formal Total Syntheses of Pteroenone and Antillatoxin
Original language description
A comparative study of the catalytic allylations and crotylations of (E)-and (Z)-haloacrylaldehydes by Lewis bases (chiral N,N'-dioxides) and Bronsted acids (chiral phosphoric acids) was undertaken. The reactions proceeded with high enantio- and diastereoselectivities with slightly better asymmetric induction observed in the case of N,N'-dioxide catalysis. The formed enantioenriched chiral unsaturated haloalcohols could be considered general building blocks, as they could be used in the syntheses of more complex natural products possessing substituted 1,3-diene fragments. This was exemplified by the formal total syntheses of pteronenone and antillatoxin.
Czech name
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Czech description
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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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Project
<a href="/en/project/GAP207%2F11%2F0587" target="_blank" >GAP207/11/0587: Development and Application of Catalysts Based on Chiral Bipyridine Scaffold</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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