Raising the diversity of Ugi reactions through selective alkylations and allylations of Ugi adducts

Alaa Zidan; Abeer M. El-Naggar; Nour E.A.Abd El-Sattar; Ali Khalil Ali; Laurent El Kaïm

doi:10.3389/fchem.2019.00020

Raising the diversity of Ugi reactions through selective alkylations and allylations of Ugi adducts

Alaa Zidan
, Abeer M. El-Naggar
, Nour E.A.Abd El-Sattar
, Ali Khalil Ali
, Laurent El Kaïm

Université Paris-Saclay
Ain-Shams University

Résultats de recherche: Contribution à un journal › Article › Revue par des pairs

Résumé

We report here selective Tsuji-Trost type allylation of Ugi adducts using a strategy based on the enhanced nucleophilicity of amide dianions. Ugi adducts derived from aromatic aldehydes were easily allylated at their peptidyl position with allyl acetate in the presence of palladium catalysts. These substitutions were compared to more classical transition metal free allylations using allyl bromides.

langue originale	Anglais
Numéro d'article	20
journal	Frontiers in Chemistry
Volume	7
Numéro de publication	JAN
Les DOIs	https://doi.org/10.3389/fchem.2019.00020
état	Publié - 1 janv. 2019
Modification externe	Oui

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10.3389/fchem.2019.00020

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title = "Raising the diversity of Ugi reactions through selective alkylations and allylations of Ugi adducts",

abstract = "We report here selective Tsuji-Trost type allylation of Ugi adducts using a strategy based on the enhanced nucleophilicity of amide dianions. Ugi adducts derived from aromatic aldehydes were easily allylated at their peptidyl position with allyl acetate in the presence of palladium catalysts. These substitutions were compared to more classical transition metal free allylations using allyl bromides.",

keywords = "Allylation, Metathesis, Palladium, Piperidines, Tsuji-Trost reaction, Ugi reaction",

author = "Alaa Zidan and El-Naggar, \{Abeer M.\} and El-Sattar, \{Nour E.A.Abd\} and Ali, \{Ali Khalil\} and \{El Ka{\"i}m\}, Laurent",

note = "Publisher Copyright: {\textcopyright} 2019 Zidan, El-Naggar, Abd El-Sattar, Ali and El Ka{\"i}m.",

year = "2019",

month = jan,

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doi = "10.3389/fchem.2019.00020",

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T1 - Raising the diversity of Ugi reactions through selective alkylations and allylations of Ugi adducts

AU - Zidan, Alaa

AU - El-Naggar, Abeer M.

AU - El-Sattar, Nour E.A.Abd

AU - Ali, Ali Khalil

AU - El Kaïm, Laurent

PY - 2019/1/1

Y1 - 2019/1/1

N2 - We report here selective Tsuji-Trost type allylation of Ugi adducts using a strategy based on the enhanced nucleophilicity of amide dianions. Ugi adducts derived from aromatic aldehydes were easily allylated at their peptidyl position with allyl acetate in the presence of palladium catalysts. These substitutions were compared to more classical transition metal free allylations using allyl bromides.

AB - We report here selective Tsuji-Trost type allylation of Ugi adducts using a strategy based on the enhanced nucleophilicity of amide dianions. Ugi adducts derived from aromatic aldehydes were easily allylated at their peptidyl position with allyl acetate in the presence of palladium catalysts. These substitutions were compared to more classical transition metal free allylations using allyl bromides.

KW - Allylation

KW - Metathesis

KW - Palladium

KW - Piperidines

KW - Tsuji-Trost reaction

KW - Ugi reaction

UR - https://www.scopus.com/pages/publications/85061186868

U2 - 10.3389/fchem.2019.00020

DO - 10.3389/fchem.2019.00020

M3 - Article

AN - SCOPUS:85061186868

SN - 2296-2646

VL - 7

JO - Frontiers in Chemistry

JF - Frontiers in Chemistry

IS - JAN

M1 - 20

ER -

Raising the diversity of Ugi reactions through selective alkylations and allylations of Ugi adducts

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