The six-membered annulation reaction involving sequential palladium-catalyzed allylic alkylation and Michael addition: scope and limitations

Unprecedented tandem allylic alkylation/intermolecular Michael addition was used in the preparation of novel bicyclic azalides. NMR spectroscopy was used not only to unambiguously determine and characterize the structures of these unexpected products of chemical reaction but also to investigate the effect the rigid bicyclic modification has on the conformation of the whole molecule. Thus, some of the macrolides prepared showed antibacterial activity in the range of well-known antibiotic drug azithromycin.

Download Full-text

The Six-Membered Annulation Reaction Involving Sequential Palladium-Catalyzed Allylic Alkylation and Michael Addition: Scope and Limitations.

ChemInform ◽

10.1002/chin.200328084 ◽

2003 ◽

Vol 34 (28) ◽

Author(s):

Celine Jousse-Karinthi ◽

Fatima Zouhiri ◽

Jacqueline Mahuteau ◽

Didier Desmaele

Keyword(s):

Michael Addition ◽

Allylic Alkylation ◽

Palladium Catalyzed

Download Full-text

Ligand-Enabled γ-C(sp3)–H Olefination of Free Carboxylic Acids

10.26434/chemrxiv.11857857 ◽

2020 ◽

Author(s):

Kiron Kumar Ghosh ◽

Alexander Uttry ◽

Francesca Ghiringhelli ◽

Arup Mondal ◽

Manuel van Gemmeren

Keyword(s):

Reaction Mechanism ◽

Carboxylic Acids ◽

Michael Addition ◽

Kinetic Studies ◽

Wide Range ◽

Palladium Catalyzed

We report the ligand enabled C(sp3)–H activation/olefination of free carboxylic acids in the γ-position. Through an intramolecular Michael-addition, δ-lactones are obtained as products. Two distinct ligand classes are identified that enable the challenging palladium-catalyzed activation of free carboxylic acids in the γ-position. The developed protocol features a wide range of acid substrates and olefin reaction partners and is shown to be applicable on a preparatively useful scale. Insights into the underlying reaction mechanism obtained through kinetic studies are reported.<br>

Download Full-text

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

Current Organic Chemistry ◽

10.2174/1385272823666190624145039 ◽

2019 ◽

Vol 23 (11) ◽

pp. 1168-1213 ◽

Cited By ~ 4

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.

Download Full-text