Chiral Unsymmetrically Substituted Bipyridine N,N-Dioxides as Catalysts for the Allylation of Aldehydes
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F18%3A00495570" target="_blank" >RIV/61388963:_____/18:00495570 - isvavai.cz</a>
Alternative codes found
RIV/00216208:11310/18:10383302
Result on the web
<a href="http://dx.doi.org/10.1002/ejoc.201800485" target="_blank" >http://dx.doi.org/10.1002/ejoc.201800485</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201800485" target="_blank" >10.1002/ejoc.201800485</a>
Alternative languages
Result language
angličtina
Original language name
Chiral Unsymmetrically Substituted Bipyridine N,N-Dioxides as Catalysts for the Allylation of Aldehydes
Original language description
A series of unsymmetrically substituted diastereoisomeric (R-a,R) and (S-a,R) bipyridine N,N-dioxides was synthesized by using oxidative coupling of the corresponding metallated tetrahydroisoquinoline N-oxides in the presence of iodine. The N,N-dioxides contained substituted aryl groups with electron-donating or electron-accepting groups in the near vicinity of the N,N-dioxide moiety. Their catalytic activity was tested in a series of reactions of allyltrichlorosilane with various substituted benzaldehydes, thiophenecarbaldehyde, and cinnamaldehyde. The reactions proceeded with high enantioselectivities (up to 98% ee) with catalyst loadings as low as 0.5 mol-%. Furthermore, allylation reactions of (E)-3-iodomethacrylaldehyde were also carried out to give chiral (E)-1-iodo-2-methylpenta-1,4-dien-3-ol, a convenient building block for the synthesis of natural products. The allylations proceeded with high enantioselectivities (up to ca. 99% ee) with a catalyst loading of 2.5 mol-%.
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/GA17-07707S" target="_blank" >GA17-07707S: Development of New Syntheses of Azaheterocycles</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2018
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
European Journal of Organic Chemistry
ISSN
1434-193X
e-ISSN
—
Volume of the periodical
2018
Issue of the periodical within the volume
37
Country of publishing house
DE - GERMANY
Number of pages
8
Pages from-to
5109-5116
UT code for WoS article
000446662900005
EID of the result in the Scopus database
2-s2.0-85050502907