Lewis Acid Assisted Chiral Bronsted Acid for Enantioselective Protonation of Silyl Enol Ethers and Ketene Bis(trialkylsilyl) Acetals

1994 ◽  
Vol 116 (24) ◽  
pp. 11179-11180 ◽  
Author(s):  
Kazuaki Ishihara ◽  
Masanobu Kaneeda ◽  
Hisashi Yamamoto
Keyword(s):  
Lewis Acid ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Brönsted Acid ◽  
Chiral Bronsted Acid

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.

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.

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