Cooperative Asymmetric Catalysis by N-Heterocyclic Carbenes and Brønsted Acid in γ-Lactam Formation: Insights into Mechanism and Stereoselectivity

ACS Catalysis ◽  
2016 ◽  
Vol 6 (5) ◽  
pp. 3118-3126 ◽  
Author(s):  
Monika Pareek ◽  
Raghavan B. Sunoj
Keyword(s):  
Asymmetric Catalysis ◽  
Heterocyclic Carbenes ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid

scholarly journals N-Heterocyclic carbene/Brønsted acid cooperative catalysis as a powerful tool in organic synthesis

2012 ◽  
Vol 8 ◽  
pp. 398-402 ◽  
Author(s):  
Rob De Vreese ◽  
Matthias D’hooghe
Keyword(s):  
Organic Chemistry ◽  
Organic Synthesis ◽  
Stereoselective Synthesis ◽  
Heterocyclic Carbenes ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Heterocyclic Chemistry ◽  
The Past ◽  
Cooperative Catalysis ◽  
Brönsted Acid

The interplay between metals and N-heterocyclic carbenes (NHCs) has provided a window of opportunities for the development of novel catalytic strategies within the past few years. The recent successful combination of Brønsted acids with NHCs has added a new dimension to the field of cooperative catalysis, enabling the stereoselective synthesis of functionalized pyrrolidin-2-ones as valuable scaffolds in heterocyclic chemistry. This Commentary will briefly highlight the concept of N-heterocyclic carbene/Brønsted acid cooperative catalysis as a new and powerful methodology in organic chemistry.

Catalytic Lewis and Brønsted acid syn-diastereoselective benzylic substitutions of α-hydroxy-β-nitro- and α-hydroxy-β-azido-alkyl arenes

2020 ◽  
Vol 98 (6) ◽  
pp. 292-306
Author(s):  
Raphaël Hensienne ◽  
Jean-Philippe Cusson ◽  
Étienne Chénard ◽  
Stephen Hanessian
Keyword(s):  
Transition State ◽  
Asymmetric Catalysis ◽  
Amino Alcohol ◽  
Chiral Ligands ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Benzylic Alcohols ◽  
New Synthesis ◽  
Brönsted Acid ◽  
State Models

A series of alkyl and alkenyl p-methoxy arenes containing α,β-disubstituted diamino and amino alcohol groups were synthesized from β-nitro and β-azido benzylic alcohols in the presence of AuCl3 as catalyst. The formation of predominantly syn-disubstituted products were rationalized on the basis of mechanistic considerations and transition state models relying on A1,3-allylic strain. The products could have utility in the design of medicinally relevant compounds and as chiral ligands for asymmetric catalysis. A new synthesis of (+)-sertraline (Zoloft) was achieved.

scholarly journals Nickel/brønsted acid dual-catalyzed regio- and enantioselective hydrophosphinylation of 1,3-dienes: access to chiral allylic phosphine oxides

2022 ◽  
Author(s):  
Jiao Long ◽  
Yuqiang Li ◽  
Weining Zhao ◽  
Guoyin Yin
Keyword(s):  
Asymmetric Catalysis ◽  
Organophosphorus Compounds ◽  
Synthetic Methods ◽  
Bioactive Molecules ◽  
Phosphine Oxides ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid

While chiral allylic organophosphorus compounds are widely utilized in asymmetric catalysis and bioactive molecules, their synthetic methods are still very limited. We report the development of an asymmetric nickel/brønsted acid...

Solvent-Free Acetalization of Glycerol with n-Octanal using Combined Brønsted Acid-Surfactant Catalyst

2017 ◽  
Vol 54 (1) ◽  
pp. 54-63 ◽  
Author(s):  
Xu Li ◽  
Lan Wu ◽  
Qiong Tang ◽  
Jinxiang Dong
Keyword(s):  
Solvent Free ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid

Synthetic Scope of Brønsted Acid-Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate

2021 ◽  
Author(s):  
Mizzanoor Rahaman ◽  
M. Shahnawaz Ali ◽  
Khorshada Jahan ◽  
Damon Hinz ◽  
Jawad Bin Belayet ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Ethyl Diazoacetate ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Catalyzed Reactions
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