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.

Design of Brønsted Acid-Assisted Chiral Brønsted Acid Catalyst Bearing a Bis(triflyl)methyl Group for a Mannich-Type Reaction

2006 ◽  
Vol 8 (15) ◽  
pp. 3175-3178 ◽  
Author(s):  
Aiko Hasegawa ◽  
Yuki Naganawa ◽  
Makoto Fushimi ◽  
Kazuaki Ishihara ◽  
Hisashi Yamamoto
Keyword(s):  
Acid Catalyst ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Methyl Group ◽  
Type Reaction ◽  
Brönsted Acid ◽  
Brønsted Acid Catalyst ◽  
Chiral Bronsted Acid ◽  
Brönsted Acid Catalyst

Hydrogen Bonds-Enabled Design of a C1-Symmetric Chiral Brønsted Acid Catalyst

ACS Catalysis ◽  
2016 ◽  
Vol 6 (2) ◽  
pp. 949-956 ◽  
Author(s):  
Norie Momiyama ◽  
Kosuke Funayama ◽  
Hirofumi Noda ◽  
Masahiro Yamanaka ◽  
Naohiko Akasaka ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Acid Catalyst ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Brønsted Acid Catalyst ◽  
Chiral Bronsted Acid ◽  
Brönsted Acid Catalyst
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