ChemInform Abstract: Boronic Acid Catalysis for Mild and Selective [3 + 2] Dipolar Cycloadditions to Unsaturated Carboxylic Acids.

ChemInform ◽  
2010 ◽  
Vol 41 (38) ◽  
pp. no-no
Author(s):  
Hongchao Zheng ◽  
Robert McDonald ◽  
Dennis G. Hall
Keyword(s):  
Carboxylic Acids ◽  
Boronic Acid ◽  
Acid Catalysis ◽  
Dipolar Cycloadditions ◽  
Unsaturated Carboxylic Acids

Scalable Synthesis of a Chiral Selenium π-Acid Catalyst and Its Use in Enantioselective Iminolactonization of β,γ-Unsaturated Amides

Synlett ◽  
2019 ◽  
Vol 30 (14) ◽  
pp. 1679-1682 ◽  
Author(s):  
Yuta Otsuka ◽  
Yuto Shimazaki ◽  
Hitoshi Nagaoka ◽  
Keiji Maruoka ◽  
Takuya Hashimoto
Keyword(s):  
Carboxylic Acids ◽  
Asymmetric Catalysis ◽  
Acid Catalysis ◽  
Acid Catalyst ◽  
Oxidative Cyclization ◽  
Unsaturated Carboxylic Acids ◽  
Long Time ◽  
Scalable Synthesis ◽  
Enantioselective Catalysts

Chiral selenium π-acid catalysis has for a long time been lagging behind other areas of asymmetric catalysis due to a lack of highly enantioselective catalysts. In this regard, we recently developed the first chiral selenium π-acid catalyst which performs the oxidative cyclization of β,γ-unsaturated carboxylic acids with high enantioselectivities. We report herein our improved synthesis of this chiral selenium catalyst, which allows access to a large quantity of the catalyst as the diselenide. In addition, the catalyst is tested in the oxidative cyclization of N-methoxy β,γ-unsaturated amides to give iminolactones with high enantioselectivities.

Enantioselective 1,4‐Addition Reaction of α,β‐Unsaturated Carboxylic Acids with Cycloalkanones Using Cooperative Chiral Amine–Boronic Acid Catalysts

2020 ◽  
Vol 132 (39) ◽  
pp. 17409-17413
Author(s):  
Takahiro Horibe ◽  
Takashi Hazeyama ◽  
Yuto Nakata ◽  
Kazuki Takeda ◽  
Kazuaki Ishihara
Keyword(s):  
Carboxylic Acids ◽  
Boronic Acid ◽  
Addition Reaction ◽  
Acid Catalysts ◽  
Chiral Amine ◽  
Unsaturated Carboxylic Acids
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