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

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Article number	20
Journal	Frontiers in Chemistry
Volume	7
Issue number	JAN
DOIs	https://doi.org/10.3389/fchem.2019.00020
Publication status	Published - 1 Jan 2019
Externally published	Yes

Keywords

Allylation
Metathesis
Palladium
Piperidines
Tsuji-Trost reaction
Ugi reaction

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10.3389/fchem.2019.00020

Cite this

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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",

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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

Abstract

Keywords

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