scholarly journals Regio- and stereospecific rhodium-catalyzed allylic alkylation with an acyl anion equivalent: an approach to acyclic α-ternary β,γ-unsaturated aryl ketones

2017 ◽  
Vol 8 (5) ◽  
pp. 4001-4005 ◽  
Author(s):  
Ben W. H. Turnbull ◽  
Jungha Chae ◽  
Samuel Oliver ◽  
P. Andrew Evans
Keyword(s):  
Allylic Alkylation ◽  
Direct Construction ◽  
Acyl Anion ◽  
Aryl Ketones

The regio- and stereospecific rhodium-catalyzed allylic alkylation of secondary allylic carbonates with cyanohydrin pronucleophiles facilitates the direct construction of acyclic α-ternary β,γ-unsaturated aryl ketones.

Palladium-Catalyzed Asymmetric Allylic Alkylation of α-Aryl Ketones.

ChemInform ◽  
2003 ◽  
Vol 34 (2) ◽  
Author(s):  
Barry M. Trost ◽  
Gretchen M. Schroeder ◽  
Jesper Kristensen
Keyword(s):  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation ◽  
Aryl Ketones ◽  
Palladium Catalyzed

scholarly journals Intermolecular Stereoselective Iridium-Catalyzed Allylic Alkylation: An Evolutionary Account

Synlett ◽  
2018 ◽  
Vol 29 (19) ◽  
pp. 2481-2492 ◽  
Author(s):  
Brian Stoltz ◽  
Samantha Shockley ◽  
J. Hethcox
Keyword(s):  
Palladium Catalysts ◽  
Allylic Alkylation ◽  
Direct Construction ◽  
Iridium Catalysts ◽  
Quaternary Centers ◽  
Evolutionary Account ◽  
Palladium Catalyzed ◽  
Quaternary Stereocenters ◽  
Quaternary Stereocenter ◽  
Alkylation Reactions

Our lab has long been interested in the development of methods for the creation of enantioenriched all-carbon quaternary stereocenters. Historically, our interest has centered on palladium-catalyzed allylic alkylation, though recent efforts have moved to include the study of iridium catalysts. Whereas palladium catalysts enable the preparation of isolated stereocenters, the use of iridium catalysts allows for the direct construction of vicinal stereocenters via an enantio-, diastereo-, and regioselective allylic alkylation. This Account details the evolution of our research program from inception, which focused on the first iridium-catalyzed allylic alkylation to prepare stereodyads containing a single quaternary stereocenter, to our most recent discovery that allows for the synthesis of vicinal quaternary centers.1 Introduction2 Synthesis of Vicinal Tertiary and All-Carbon Quaternary Stereocenters via Enantio- and Diastereoselective Iridium-Catalyzed Allylic Alkylation2.1 Cyclic Nucleophiles2.2 Acyclic Nucleophiles2.3 Alkyl-Substituted Electrophiles3 Umpoled Iridium-Catalyzed Allylic Alkylation Reactions3.1 Tertiary Allylic Stereocenters3.2 Quaternary Allylic Stereocenters4 Synthesis of Vicinal All-Carbon Quaternary Centers via Enantio­selective Iridium-Catalyzed Allylic Alkylation5 Summary and Future Outlook

scholarly journals Acetoxy Meldrum’s Acid: A Versatile Acyl Anion Equivalent in the Pd-Catalyzed Asymmetric Allylic Alkylation

2011 ◽  
Vol 13 (12) ◽  
pp. 3222-3225 ◽  
Author(s):  
Barry M. Trost ◽  
Maksim Osipov ◽  
Philip S. J. Kaib ◽  
Mark T. Sorum
Keyword(s):  
Allylic Alkylation ◽  
Meldrum's Acid ◽  
Meldrum’S Acid ◽  
Asymmetric Allylic Alkylation ◽  
Acyl Anion

Ni(0)-Catalyzed α-Allylic Alkylation of Regular Ketones with 1,3-Dienes under pH and Redox-neutral Conditions

2019 ◽  
Author(s):  
Tiantian Chen ◽  
Yang Yang ◽  
Liyu Xie ◽  
Haijian Yang ◽  
Guangbin Dong ◽  
...  
Keyword(s):  
Oxidative Addition ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Dual Role ◽  
Allylic Alkylation ◽  
Cross Coupling Reaction ◽  
Neutral Conditions

<p>We report a Ni(0)-catalyzed cross coupling reaction between simple ketones and 1,3-dienes. A variety of a-allylic alkylation products were formed in an 1,2-addition manner with excellent regioselectivity. Water was found to significantly accelerate this transformation. A HO-Ni-H species generated from oxidative addition of Ni(0) to H<sub>2</sub>O is proposed to play a “dual role” in activating both the ketone and the diene substrate.</p>

Direct Construction and Screening of the Expression Vector of Anaerobic Clostridium in Escherichia coli

2013 ◽  
Vol 19 (5) ◽  
pp. 822-826
Author(s):  
Chunyu LIU ◽  
Yan CHEN ◽  
Jinqun HUANG ◽  
Jianxin PEI ◽  
Hao PANG ◽  
...  
Keyword(s):  
Escherichia Coli ◽  
Expression Vector ◽  
Direct Construction

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.

The Merger of CF3SO2Na and Palladium Catalysis to Enable Decarboxylative Cross-Coupling for the Synthesis of Aromatic Ketones under Room Temperature

2021 ◽  
Author(s):  
Pan Xie ◽  
Cheng Xue ◽  
Cancan Wang ◽  
Dongdong Du ◽  
Sanshan Shi
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Palladium Catalysis ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Aromatic Ketones ◽  
Aryl Ketones ◽  
Oxocarboxylic Acids

A CF3SO2Na/Pd(OAc)2 co-catalyzed strategy is developed to produce aryl ketones via visible-light-induced decarboxylative cross-coupling of α-oxocarboxylic acids and aryl boronic acids. This process was perfomed under air at room temperature,...

Sign in / Sign up

Export Citation Format

Share Document