scholarly journals Palladium-Catalyzed Allylic Alkylation of Carboxylic Acid Derivatives: N-Acyloxazolinones as Ester Enolate Equivalents

2011 ◽  
Vol 51 (1) ◽  
pp. 204-208 ◽  
Author(s):  
Barry M. Trost ◽  
David J. Michaelis ◽  
Julie Charpentier ◽  
Jiayi Xu
Keyword(s):  
Carboxylic Acid ◽  
Allylic Alkylation ◽  
Palladium Catalyzed ◽  
Ester Enolate

ChemInform Abstract: Palladium-Catalyzed Allylic Alkylation of Carboxylic Acid Derivatives: N-Acyloxazolinones as Ester Enolate Equivalents.

ChemInform ◽  
2012 ◽  
Vol 43 (20) ◽  
pp. no-no
Author(s):  
Barry M. Trost ◽  
David J. Michaelis ◽  
Julie Charpentier ◽  
Jiayi Xu
Keyword(s):  
Carboxylic Acid ◽  
Allylic Alkylation ◽  
Palladium Catalyzed ◽  
Ester Enolate

scholarly journals Palladium-Catalyzed Allylic Alkylation of Carboxylic Acid Derivatives: N-Acyloxazolinones as Ester Enolate Equivalents

2011 ◽  
Vol 124 (1) ◽  
pp. 208-212 ◽  
Author(s):  
Barry M. Trost ◽  
David J. Michaelis ◽  
Julie Charpentier ◽  
Jiayi Xu
Keyword(s):  
Carboxylic Acid ◽  
Allylic Alkylation ◽  
Palladium Catalyzed ◽  
Ester Enolate

scholarly journals Palladium-Catalyzed Asymmetric Allylic Alkylation of 2-Acylimidazoles as Ester Enolate Equivalents

2010 ◽  
Vol 132 (26) ◽  
pp. 8915-8917 ◽  
Author(s):  
Barry M. Trost ◽  
Konrad Lehr ◽  
David J. Michaelis ◽  
Jiayi Xu ◽  
Andreas K. Buckl
Keyword(s):  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation ◽  
Palladium Catalyzed ◽  
Ester Enolate

ChemInform Abstract: Palladium-Catalyzed Asymmetric Allylic Alkylation of 2-Acylimidazoles as Ester Enolate Equivalents.

ChemInform ◽  
2010 ◽  
Vol 41 (52) ◽  
pp. no-no
Author(s):  
Barry M. Trost ◽  
Konrad Lehr ◽  
David J. Michaelis ◽  
Jiayi Xu ◽  
Andreas K. Buckl
Keyword(s):  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation ◽  
Palladium Catalyzed ◽  
Ester Enolate

Stereospecific, Palladium-catalyzed C(sp3)–H Alkenylation and Alkynylation of a Proline Derivative Enabled by 8-Aminoquinoline as a Directing Group

2020 ◽  
Author(s):  
Aleksandra Balliu ◽  
Aaltje Roelofje Femmigje Strijker ◽  
Michael Oschmann ◽  
Monireh Pourghasemi Lati ◽  
Oscar Verho
Keyword(s):  
Carboxylic Acid ◽  
Building Blocks ◽  
Wide Range ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
High Yields ◽  
Vinyl Iodides ◽  
Initial Results

<p>In this preprint, we present our initial results concerning a stereospecific Pd-catalyzed protocol for the C3 alkenylation and alkynylation of a proline derivative carrying the well utilized 8‑aminoquinoline directing group. Efficient C–H alkenylation was achieved with a wide range of vinyl iodides bearing different aliphatic, aromatic and heteroaromatic substituents, to furnish the corresponding C3 alkenylated products in good to high yields. In addition, we were able show that this protocol can also be used to install an alkynyl group into the pyrrolidine scaffold, when a TIPS-protected alkynyl bromide was used as the reaction partner. Furthermore, two different methods for the removal of the 8-aminoquinoline auxiliary are reported, which can enable access to both <i>cis</i>- and <i>trans</i>-configured carboxylic acid building blocks from the C–H alkenylation products.</p>

Novel Chiral Ligands for Palladium-catalyzed Asymmetric Allylic Alkylation/ Asymmetric Tsuji-Trost Reaction: A Review

2019 ◽  
Vol 23 (11) ◽  
pp. 1168-1213 ◽  
Author(s):  
Samar Noreen ◽  
Ameer Fawad Zahoor ◽  
Sajjad Ahmad ◽  
Irum Shahzadi ◽  
Ali Irfan ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Enantioselective Synthesis ◽  
Chiral Ligands ◽  
Allylic Alkylation ◽  
Research Groups ◽  
Asymmetric Allylic Alkylation ◽  
Catalytic Potential ◽  
Long Time ◽  
Palladium Catalyzed ◽  
Alkylation Reactions

Background: Asymmetric catalysis holds a prestigious role in organic syntheses since a long time and chiral inductors such as ligands have been used to achieve the utmost desired results at this pitch. The asymmetric version of Tsuji-Trost allylation has played a crucial role in enantioselective synthesis. Various chiral ligands have been known for Pdcatalyzed Asymmetric Allylic Alkylation (AAA) reactions and exhibited excellent catalytic potential. The use of chiral ligands as asymmetric inductors has widened the scope of Tsuji-Trost allylic alkylation reactions. Conclusion: Therefore, in this review article, a variety of chiral inductors or ligands have been focused for palladium catalyzed asymmetric allylic alkylation (Tsuji-Trost allylation) and in this regard, recently reported literature (2013-2017) has been described. The use of ligands causes the induction of enantiodiscrimination to the allylated products, therefore, the syntheses of various kinds of ligands have been targeted by many research groups to employ in Pd-catalyzed AAA reactions.

Palladium-catalyzed decarboxylative allylic alkylation of allylic acetates with .beta.-keto acids

1986 ◽  
Vol 51 (4) ◽  
pp. 421-426 ◽  
Author(s):  
Tetsuo Tsuda ◽  
Masahiro Okada ◽  
Seiichi Nishi ◽  
Takeo Saegusa
Keyword(s):  
Allylic Alkylation ◽  
Keto Acids ◽  
Palladium Catalyzed

New Access to Kainic Acid via Intramolecular Palladium-Catalyzed Allylic Alkylation

Synlett ◽  
2007 ◽  
Vol 2007 (10) ◽  
pp. 1521-1524
Author(s):  
David Madec ◽  
Giovanni Poli ◽  
Mathieu Thuong ◽  
Silvia Sottocornola ◽  
Guillaume Prestat ◽  
...  
Keyword(s):  
Kainic Acid ◽  
Allylic Alkylation ◽  
Palladium Catalyzed
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