Brønsted acid mediated N–O bond cleavage for α-amination of ketones through the aromatic nitroso aldol reaction

2016 ◽  
Vol 52 (15) ◽  
pp. 3215-3218 ◽  
Author(s):  
Isai Ramakrishna ◽  
Harekrishna Sahoo ◽  
Mahiuddin Baidya
Keyword(s):  
Bond Cleavage ◽  
Aldol Reaction ◽  
Nitroso Compounds ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Brönsted Acid ◽  
Aromatic Nitroso Compounds

A Brønsted acid mediated N–O bond cleavage for α-amination of ketones has been developed through the nitroso aldol reaction of less-reactive aromatic nitroso compounds and silyl enol ethers having a disilane (–SiMe2TMS) backbone.

Enantioselective Protonation of Silyl Enol Ethers Catalyzed by a Chiral Pentacarboxycyclopentadiene-Based Brønsted Acid

Synlett ◽  
2019 ◽  
Vol 30 (11) ◽  
pp. 1317-1320 ◽  
Author(s):  
Jun Li ◽  
Shaoyu An ◽  
Chao Yuan ◽  
Pingfan Li
Keyword(s):  
Acid Catalyst ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Brönsted Acid ◽  
Brønsted Acid Catalyst ◽  
Proton Source ◽  
Aryl Ketones ◽  
Chiral Bronsted Acid

The enantioselective protonation of silyl enol ethers was realized in the presence of a pentacarboxycyclopenta-1,3-diene-based chiral Brønsted acid catalyst with water as an achiral proton source to give the corresponding α-aryl ketones in good yields and up to 75% ee.

Synthesis of 1-Alkyl-3-(2-oxo-2-aryl/alkyl-ethyl)indolin-2-ones through Gold/Brønsted Acid Relay Actions: Observation of Selective C=C Bond Cleavage of Enaminones

Synthesis ◽  
2017 ◽  
Vol 49 (16) ◽  
pp. 3609-3618 ◽  
Author(s):  
Yanzhong Li ◽  
Yulei Zhao ◽  
Yang Yuan ◽  
Lingkai Kong ◽  
Fangfang Zhang
Keyword(s):  
Reaction Mechanism ◽  
Bond Cleavage ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Reaction Conditions ◽  
One Pot ◽  
Esi Ms ◽  
Ms Analysis ◽  
Brönsted Acid

A novel gold(I)/Brønsted acid sequential catalyzed/promoted procedure to synthesize 1-alkyl-3-(2-oxo-2-aryl/alkyl-ethyl)indolin-2-ones under mild reaction conditions is developed. This methodology is realized by relay actions of gold and a Brønsted acid in a one-pot multistep manner. The gold(I)-catalyzed chemoselective C(sp2)-H functionalization of enaminones and Brønsted acid promoted cleavage of the C=C bond are integrated effectively. Based on the results of control experiments and ESI-MS analysis, a possible reaction mechanism is proposed.

Domino construction of a bullataketal core via double bond cleavage in activated dihydrofurans

2018 ◽  
Vol 5 (10) ◽  
pp. 1655-1663 ◽  
Author(s):  
Konstantin L. Ivanov ◽  
Ivan M. Vatsouro ◽  
Stanislav I. Bezzubov ◽  
Mikhail Ya. Melnikov ◽  
Ekaterina M. Budynina
Keyword(s):  
Double Bond ◽  
Bond Cleavage ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Biologically Relevant ◽  
Brönsted Acid

A new rapid approach to structurally challenging and biologically relevant methanobenzodioxepines was developed via a Brønsted acid-triggered domino transformation of 3-carbonyl-4,5-dihydrofurans, substituted with MOM-protected o-hydroxyaryls at the C4 atom.

scholarly journals Brønsted Acid Catalyzed Asymmetric Aldol Reaction: A Complementary Approach to Enamine Catalysis

2010 ◽  
Vol 12 (16) ◽  
pp. 3582-3585 ◽  
Author(s):  
Guillaume Pousse ◽  
Fabien Le Cavelier ◽  
Luke Humphreys ◽  
Jacques Rouden ◽  
Jérôme Blanchet
Keyword(s):  
Aldol Reaction ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Asymmetric Aldol ◽  
Complementary Approach ◽  
Brönsted Acid ◽  
Asymmetric Aldol Reaction ◽  
Enamine Catalysis ◽  
Acid Catalyzed
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