Highly Regio‐, Diastereo‐, and Enantioselective Synthesis of Tetrahydroazepines and Benzo[ b ]oxepines through Palladium‐Catalyzed [4+3] Cycloaddition Reactions

2019 ◽  
Vol 132 (3) ◽  
pp. 1259-1263 ◽  
Author(s):  
Barry M. Trost ◽  
Zhijun Zuo
Keyword(s):  
Enantioselective Synthesis ◽  
Cycloaddition Reactions ◽  
Palladium Catalyzed

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.

scholarly journals Direct access to spirocycles by Pd/WingPhos-catalyzed enantioselective cycloaddition of 1,3-enynes

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Long Li ◽  
Shan Wang ◽  
Pengfei Luo ◽  
Ran Wang ◽  
Zheng Wang ◽  
...  
Keyword(s):  
Drug Discovery ◽  
Functional Groups ◽  
Organic Synthesis ◽  
Enantioselective Synthesis ◽  
Direct Access ◽  
Cycloaddition Reactions ◽  
Drug Discovery And Development ◽  
Spirocyclic Compounds ◽  
And Control ◽  
By Products

AbstractSpirocycles play an important role in drug discovery and development. The direct, catalytic, and enantioselective synthesis of spirocycles from readily available starting materials and in an atom economic manner remains a highly sought-after task in organic synthesis. Herein, an enantioselective Pd-hydride-catalyzed cycloaddition method for the synthesis of spirocyclic compounds directly from two classes of commonly available starting materials, 1,3-enynes and cyclic carbon−hydrogen (C−H) bonds, is reported. The reactions employ a chiral Pd/WingPhos catalyst to both suppress the formation of bis-allenyl by-products and control the stereoselectivity. 1,3-Enynes are used as dielectrophilic four-carbon units in the cycloaddition reactions, which also enables an enyne substrate-directed enantioselectivity switch with good levels of stereocontrol. The present spirocycle synthesis tolerates a broad range of functional groups of 1,3-enyne substrates, including alcohols, esters, nitriles, halides, and olefins. A variety of diverse cyclic nucleophiles, including pharmaceutically important heterocycles and carbocycles, can be flexibly incorporated with spiro scaffolds.

Enantioselective Synthesis of β-Trifluoromethyl-β-lactones via NHC-Catalyzed Ketene−Ketone Cycloaddition Reactions

2009 ◽  
Vol 11 (18) ◽  
pp. 4029-4031 ◽  
Author(s):  
Xiao-Na Wang ◽  
Pan-Lin Shao ◽  
Hui Lv ◽  
Song Ye
Keyword(s):  
Enantioselective Synthesis ◽  
Cycloaddition Reactions

Palladium-Catalyzed Enantioselective Synthesis of Cyclic Sulfamidates and Application to a Synthesis of Verubecestat

2018 ◽  
Vol 20 (5) ◽  
pp. 1265-1268 ◽  
Author(s):  
Wenyong Chen ◽  
Dongfang Meng ◽  
Blaise N’Zemba ◽  
William J. Morris
Keyword(s):  
Enantioselective Synthesis ◽  
Palladium Catalyzed
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