Synthesis of P-Chirogenic Diarylphosphinoacetic Acids and Their Proline Derivatives for Palladium-Catalyzed Allylic Alkylation Reactions.

ChemInform ◽  
2006 ◽  
Vol 37 (10) ◽  
Author(s):  
Hubert Lam ◽  
Peter N. Horton ◽  
Michael B. Hursthouse ◽  
David J. Aldous ◽  
King Kuok Hii
Keyword(s):  
Allylic Alkylation ◽  
Palladium Catalyzed ◽  
Proline Derivatives ◽  
Alkylation Reactions

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.

Synthesis of highly rigid phosphine–oxazoline ligands for palladium-catalyzed asymmetric allylic alkylation

2018 ◽  
Vol 16 (41) ◽  
pp. 7717-7724 ◽  
Author(s):  
Zhongxuan Qiu ◽  
Rui Sun ◽  
Dawei Teng
Keyword(s):  
Catalytic Performance ◽  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation ◽  
Palladium Catalyzed ◽  
Alkylation Reactions ◽  
Stereogenic Center ◽  
Oxazoline Ligands ◽  
Excellent Catalytic Performance

Rigid phosphine–oxazoline ligands with a spirocarbon stereogenic center were developed, which exhibited excellent catalytic performance for Pd-catalyzed allylic alkylation reactions.

scholarly journals Bulky Monodentate Phosphoramidites in Palladium-Catalyzed Allylic Alkylation Reactions: Aspects of Regioselectivity and Enantioselectivity

2004 ◽  
Vol 10 (24) ◽  
pp. 6232-6246 ◽  
Author(s):  
Maarten D. K. Boele ◽  
Paul C. J. Kamer ◽  
Martin Lutz ◽  
Anthony L. Spek ◽  
Johannes G. de Vries ◽  
...  
Keyword(s):  
Allylic Alkylation ◽  
Palladium Catalyzed ◽  
Alkylation Reactions

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 Enantioselective palladium-catalyzed allylic alkylation reactions in the synthesis of Aspidosperma and structurally related monoterpene indole alkaloids

2018 ◽  
Vol 35 (6) ◽  
pp. 559-574 ◽  
Author(s):  
Beau P. Pritchett ◽  
Brian M. Stoltz
Keyword(s):  
Indole Alkaloids ◽  
Allylic Alkylation ◽  
Monoterpene Indole Alkaloids ◽  
Palladium Catalyzed ◽  
Alkylation Reactions

The development of new heterocyclic substrate classes for palladium-catalyzed allylic alkylation has enhanced synthetic access to structurally diverse monoterpene indole alkaloids.

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