Enantiospecific Synthesis of Allylamines via the Regioselective Rhodium-Catalyzed Allylic Amination Reaction

1999 ◽  
Vol 121 (28) ◽  
pp. 6761-6762 ◽  
Author(s):  
P. Andrew Evans ◽  
John E. Robinson ◽  
Jade D. Nelson
Keyword(s):  
Allylic Amination ◽  
Amination Reaction ◽  
Enantiospecific Synthesis

scholarly journals Synthetic Studies on Tricyclic Diterpenoids: Direct Allylic Amination Reaction of Isopimaric Acid Derivatives

ChemistryOpen ◽  
2015 ◽  
Vol 5 (1) ◽  
pp. 65-70 ◽  
Author(s):  
Mariya A. Timoshenko ◽  
Yurii V. Kharitonov ◽  
Makhmut M. Shakirov ◽  
Irina Yu. Bagryanskaya ◽  
Elvira E. Shults
Keyword(s):  
Allylic Amination ◽  
Isopimaric Acid ◽  
Amination Reaction ◽  
Synthetic Studies

A Brønsted acid-promoted asymmetric intramolecular allylic amination of alcohols

2018 ◽  
Vol 16 (3) ◽  
pp. 380-383 ◽  
Author(s):  
Jianqiao Zhou ◽  
Hexin Xie
Keyword(s):  
Bronsted Acid ◽  
Brønsted Acid ◽  
Allylic Amination ◽  
Amination Reaction ◽  
Brönsted Acid ◽  
Chiral Bronsted Acid

An asymmetric intramolecular allylic amination reaction catalyzed by a chiral Brønsted acid is disclosed, affording biologically intriguing chiral 2-substituted hydroquinolines in up to 90% yield and with up to 93% ee.

FeCl3·6H2O and TfOH as Catalysts for Allylic Amination Reaction: A Comparative Study

2012 ◽  
Vol 2012 (15) ◽  
pp. 2929-2934 ◽  
Author(s):  
Paz Trillo ◽  
Alejandro Baeza ◽  
Carmen Nájera
Keyword(s):  
Comparative Study ◽  
Allylic Amination ◽  
Amination Reaction

scholarly journals The Mechanism of Rhodium Catalyzed Allylic C–H Amination

2019 ◽  
Author(s):  
Robert Harris ◽  
Jiyong Park ◽  
Taylor Nelson ◽  
Nafees Iqbal ◽  
Daniel Salgueiro ◽  
...  
Keyword(s):  
Acid Catalyst ◽  
Reductive Elimination ◽  
Quantum Mechanical ◽  
Allylic Amination ◽  
Reaction Conditions ◽  
Allyl Complex ◽  
Acetate Ligand ◽  
Amination Reaction ◽  
Lewis Acid Catalyst

The mechanism of catalytic allylic C–H amination reactions promoted by Cp*Rh complexes is reported. Reaction kinetics experiments, stoichiometric studies, and DFT calculations demonstrate that allylic C–H activation to generate a Cp*Rh(π-allyl) complex is viable under mild reaction conditions. The role of external oxidant in the catalytic cycle is elucidated. Quantum mechanical calculations, stoichiometric reactions, and cyclic voltammetry<b></b>experiments support an oxidatively induced reductive elimination process of the allyl fragment with an acetate ligand. Lastly, evidences supporting the amination of an allylic acetate intermediate is presented. Both nucleophilic substitution catalyzed by Ag<sup>+</sup>that behaves as a Lewis acid catalyst and an inner-sphere amination catalyzed by Cp*Rh are shown to be viable for the last step of the allylic amination reaction.

Regio- and enantioselective formation of tetrazole-bearing quaternary stereocenters via palladium-catalyzed allylic amination

2022 ◽  
Author(s):  
Shahid Khan ◽  
Yu Wang ◽  
Mei-Na Zhang ◽  
Shahida Perveen ◽  
Junjie Zhang ◽  
...  
Keyword(s):  
Cyclic Carbonates ◽  
Allylic Amination ◽  
Amination Reaction ◽  
Palladium Catalyzed ◽  
Quaternary Stereocenters ◽  
Quaternary Stereocenter

Based on palladium-catalyzed allylic amination reaction, the first general example of enantioselective formation of tetrazole-bearing quaternary stereocenter has been developed. The protocol utilizes ambivalent tetrazole and vinyl cyclic carbonates as...

Cooperativity and serial ligand catalysis in an allylic amination reaction by Pd(ii)-bis-sulfoxide and Brønsted acids

2019 ◽  
Vol 17 (33) ◽  
pp. 7723-7734
Author(s):  
Dilna B. Sreedhar ◽  
Raghavan B. Sunoj
Keyword(s):  
Catalytic Cycle ◽  
Bronsted Acids ◽  
Allylic Amination ◽  
Amination Reaction ◽  
Homoallylic Amines

Under dual catalytic conditions, the general premise of holding the native ligands on the catalyst throughout the catalytic cycle becomes immediately questionable. We have invoked the likelihood of Serial Ligand Catalysis in an important intramolecular allylic amination of N-Boc protected homoallylic amines leading to an anti-oxazolidinone product.

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