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
Identifikátory výsledku
Kód výsledku v IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F16%3A10371963" target="_blank" >RIV/00216208:11310/16:10371963 - isvavai.cz</a>
Nalezeny alternativní kódy
RIV/61388963:_____/16:00471657
Výsledek na webu
<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>
Alternativní jazyky
Jazyk výsledku
angličtina
Název v původním jazyce
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
Popis výsledku v původním jazyce
Background: Catalytic asymmetric allylation of aldehydes is a synthetically useful method for preparation of chiral homoallylic alcohols that may serve as convenient synthetic building blocks. The catalysis can be brought about with Lewis acid or Lewis bases, and Bronsted acids. Objective: The main aim was to evaluate enantioselective allylation of variously substituted alpha, beta, gamma, delta-aldehydes with allyltrichlorosilane catalyzed by axially chiral Lewis bases with bis(tetrahybis(tetrahydroisoquinoline) N, N'-dioxide scaffold. Method: 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. Results: 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 (an intermediate for synthesis of papulacandin D) with a high asymmetric induction of 92% ee. Conclusion: Enantioselective allylation of alpha, beta, gamma, delta-aldehydes with allyltrichlorosilane catalyzed by an axially chiral Lewis base gave rise to the corresponding homoallylic alcohols with a good enantioselection. This method could be used for synthesis of valuable building block for organic synthesis as it was demonstrated by a synthesis of a papulacandin D intermediate.
Název v anglickém jazyce
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
Popis výsledku anglicky
Background: Catalytic asymmetric allylation of aldehydes is a synthetically useful method for preparation of chiral homoallylic alcohols that may serve as convenient synthetic building blocks. The catalysis can be brought about with Lewis acid or Lewis bases, and Bronsted acids. Objective: The main aim was to evaluate enantioselective allylation of variously substituted alpha, beta, gamma, delta-aldehydes with allyltrichlorosilane catalyzed by axially chiral Lewis bases with bis(tetrahybis(tetrahydroisoquinoline) N, N'-dioxide scaffold. Method: 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. Results: 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 (an intermediate for synthesis of papulacandin D) with a high asymmetric induction of 92% ee. Conclusion: Enantioselective allylation of alpha, beta, gamma, delta-aldehydes with allyltrichlorosilane catalyzed by an axially chiral Lewis base gave rise to the corresponding homoallylic alcohols with a good enantioselection. This method could be used for synthesis of valuable building block for organic synthesis as it was demonstrated by a synthesis of a papulacandin D intermediate.
Klasifikace
Druh
J<sub>imp</sub> - Článek v periodiku v databázi Web of Science
CEP obor
—
OECD FORD obor
10401 - Organic chemistry
Návaznosti výsledku
Projekt
<a href="/cs/project/GAP207%2F11%2F0587" target="_blank" >GAP207/11/0587: Vývoj a využití katalyzátorů s bipyridinovým skeletem</a><br>
Návaznosti
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Ostatní
Rok uplatnění
2016
Kód důvěrnosti údajů
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Údaje specifické pro druh výsledku
Název periodika
CURRENT ORGANOCATALYSIS
ISSN
2213-3372
e-ISSN
—
Svazek periodika
3
Číslo periodika v rámci svazku
3
Stát vydavatele periodika
US - Spojené státy americké
Počet stran výsledku
5
Strana od-do
301-305
Kód UT WoS článku
000406981800008
EID výsledku v databázi Scopus
2-s2.0-85047065832