Enantioselective Allylation of Selected ortho-Substituted Benzaldehydes: A Comparative Study

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F14%3A10283180" target="_blank" >RIV/00216208:11310/14:10283180 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1002/ejoc.201403034" target="_blank" >http://dx.doi.org/10.1002/ejoc.201403034</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/ejoc.201403034" target="_blank" >10.1002/ejoc.201403034</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Enantioselective Allylation of Selected ortho-Substituted Benzaldehydes: A Comparative Study

Popis výsledku v původním jazyce

We report a systematic study of the allylation of ortho-substituted benzaldehydes under catalysis of a Lewis base (N, N-dioxide), a Lewis acid (Keck allylation), and a Bronsted acid. ortho-Halobenzaldehydes were used as the aldehydic substrates, and special attention was paid to ortho-vinyl and alkynyl benzaldehydes, which might serve as interesting synthons for the preparation of more complex chiral compounds. Similar enantioselectivities were achieved under catalytic conditions. In the case of ortho-halobenzaldehydes, Lewis base catalysis proved to be more efficient, and the highest asymmetric induction for allylation of ortho-fluorobenzaldehyde reached 82% ee, which is comparable to other used catalytic conditions. In cases of ortho-vinylbenzaldehyde, the Keck allylation provided the product in 88% ee. An enantioenriched homoallylic alcohol was used as the starting material for the synthesis of a sertraline intermediate.

Název v anglickém jazyce

Enantioselective Allylation of Selected ortho-Substituted Benzaldehydes: A Comparative Study

Popis výsledku anglicky

We report a systematic study of the allylation of ortho-substituted benzaldehydes under catalysis of a Lewis base (N, N-dioxide), a Lewis acid (Keck allylation), and a Bronsted acid. ortho-Halobenzaldehydes were used as the aldehydic substrates, and special attention was paid to ortho-vinyl and alkynyl benzaldehydes, which might serve as interesting synthons for the preparation of more complex chiral compounds. Similar enantioselectivities were achieved under catalytic conditions. In the case of ortho-halobenzaldehydes, Lewis base catalysis proved to be more efficient, and the highest asymmetric induction for allylation of ortho-fluorobenzaldehyde reached 82% ee, which is comparable to other used catalytic conditions. In cases of ortho-vinylbenzaldehyde, the Keck allylation provided the product in 88% ee. An enantioenriched homoallylic alcohol was used as the starting material for the synthesis of a sertraline intermediate.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

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

Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2014

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

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Svazek periodika

neuveden

Číslo periodika v rámci svazku

32

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

8

Strana od-do

7245-7252

Kód UT WoS článku

000344624000023

EID výsledku v databázi Scopus

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