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

Kód výsledku v 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>

Nalezeny alternativní kódy

RIV/00216208:11310/16:10371963

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>

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

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.

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

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GAP207%2F11%2F0587" target="_blank" >GAP207/11/0587: Vývoj a využití katalyzátorů s bipyridinovým skeletem</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2016

Kód důvěrnosti údajů

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

Název periodika

Current Organocatalysis

ISSN

2213-3372

e-ISSN

—

Svazek periodika

3

Číslo periodika v rámci svazku

3

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

5

Strana od-do

301-305

Kód UT WoS článku

000406981800008

EID výsledku v databázi Scopus

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