Enantioselective allylations of selected alpha, beta, gamma, delta-unsaturated aldehydes by axially chiral N,N'-dioxides. Synthesis of the left-hand part of papulacandin D
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F16%3A00471657" target="_blank" >RIV/61388963:_____/16:00471657 - isvavai.cz</a>
Alternative codes found
RIV/00216208:11310/16:10371963
Result on the web
<a href="http://dx.doi.org/10.2174/2213337203666160304193640" target="_blank" >http://dx.doi.org/10.2174/2213337203666160304193640</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.2174/2213337203666160304193640" target="_blank" >10.2174/2213337203666160304193640</a>
Alternative languages
Result language
angličtina
Original language name
Enantioselective allylations of selected alpha, beta, gamma, delta-unsaturated aldehydes by axially chiral N,N'-dioxides. Synthesis of the left-hand part of papulacandin D
Original language description
Allylations of several structurally different alpha, beta, gamma, delta-aldehydes were carried out in various solvents in the presence of a catalytic amount of an N,N’-dioxide to access conditions leading to the highest symmetric induction. Out of screening of several reaction conditions the highest asymmetric induction (up to 98% ee) was achieved in THF. A higher asymmetric induction was observed with substrates bearing additional substituents on alpha-carbon atom. Allylation of (S)-(2E,4E)-2,8-dimethyldecadienal gave rise to the corresponding homoallylic alcohol with a high asymmetric induction of 92% ee. The method is useful for synthesis of valuable building block for organic synthesis as it was demonstrated by a synthesis of a papulacandin D intermediate.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
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
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
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
Current Organocatalysis
ISSN
2213-3372
e-ISSN
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Volume of the periodical
3
Issue of the periodical within the volume
3
Country of publishing house
NL - THE KINGDOM OF THE NETHERLANDS
Number of pages
5
Pages from-to
301-305
UT code for WoS article
000406981800008
EID of the result in the Scopus database
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