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

Result code in 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>

Result on the web

<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>

Result language

angličtina

Original language name

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

Original language description

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.

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

<a href="/en/project/GAP207%2F11%2F0587" target="_blank" >GAP207/11/0587: Development and Application of Catalysts Based on Chiral Bipyridine Scaffold</a><br>

Continuities

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

Publication year

2014

Confidentiality

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

Name of the periodical

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

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Volume of the periodical

neuveden

Issue of the periodical within the volume

32

Country of publishing house

DE - GERMANY

Number of pages

8

Pages from-to

7245-7252

UT code for WoS article

000344624000023

EID of the result in the Scopus database

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