Chiral Unsymmetrically Substituted Bipyridine N,N-Dioxides as Catalysts for the Allylation of Aldehydes

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F18%3A10383302" target="_blank" >RIV/00216208:11310/18:10383302 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61388963:_____/18:00495570

Výsledek na webu

<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=5RTW0N49r-" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=5RTW0N49r-</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/ejoc.201800485" target="_blank" >10.1002/ejoc.201800485</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Chiral Unsymmetrically Substituted Bipyridine N,N-Dioxides as Catalysts for the Allylation of Aldehydes

Popis výsledku v původním jazyce

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-%.

Název v anglickém jazyce

Chiral Unsymmetrically Substituted Bipyridine N,N-Dioxides as Catalysts for the Allylation of Aldehydes

Popis výsledku anglicky

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-%.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GA17-07707S" target="_blank" >GA17-07707S: Vývoj nových syntéz azaheterocyklů</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2018

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

—

Svazek periodika

neuveden

Číslo periodika v rámci svazku

37

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

8

Strana od-do

5109-5116

Kód UT WoS článku

000446662900005

EID výsledku v databázi Scopus

2-s2.0-85050502907