Asymmetric synthesis of highly functionalized furanones via direct Michael reactions mediated by a bulky primary amine

2019 ◽  
Vol 6 (8) ◽  
pp. 1080-1083 ◽  
Author(s):  
Huicai Huang ◽  
Xue Lu ◽  
Yukang Mao ◽  
Jinxing Ye
Keyword(s):  
Asymmetric Synthesis ◽  
Primary Amine ◽  
Michael Reaction ◽  
Michael Reactions

A bulky chiral primary amine catalyzed Michael reaction of 3(2H)-furanones has been realized, leading to the construction of substituted furanone derivatives.

Primary amine catalyzed diastereo- and enantioselective Michael reaction of thiazolones and α,β-unsaturated ketones

2019 ◽  
Vol 17 (42) ◽  
pp. 9305-9312 ◽  
Author(s):  
Min Lu ◽  
Hong Li ◽  
Chuncheng Zou ◽  
Jianchang Li ◽  
Chengyu Liu ◽  
...  
Keyword(s):  
Primary Amine ◽  
Michael Reaction ◽  
Unsaturated Ketones ◽  
Michael Reactions ◽  
Amine Catalysts

Organocatalytic asymmetric Michael reactions between thiazolones and α,β-unsaturated ketones were developed. By using primary amine catalysts, the products were obtained with good to excellent yields and stereoselectivities.

Recent advances in the asymmetric synthesis of pharmacology-relevant nitrogen heterocycles via stereoselective aza-Michael reactions

2019 ◽  
Vol 17 (15) ◽  
pp. 3670-3708 ◽  
Author(s):  
Maxim G. Vinogradov ◽  
Olga V. Turova ◽  
Sergei G. Zlotin
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Reaction ◽  
Nitrogen Heterocycles ◽  
Michael Reactions ◽  
Naturally Occurring ◽  
Recent Advances

In this review, recent applications of a stereoselective aza-Michael reaction for asymmetric synthesis of naturally occurring N-containing heterocyclic scaffolds and their usefulness to pharmacology are summarized.

ChemInform Abstract: Base-Dependent Stereodivergent Intramolecular Aza-Michael Reaction: Asymmetric Synthesis of 1,3-Disubstituted Isoindolines.

ChemInform ◽  
2014 ◽  
Vol 45 (3) ◽  
pp. no-no
Author(s):  
Santos Fustero ◽  
Lidia Herrera ◽  
Ruben Lazaro ◽  
Elsa Rodriguez ◽  
Miguel A. Maestro ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Reaction

Carbonyl catalysis enables a biomimetic asymmetric Mannich reaction

Science ◽  
2018 ◽  
Vol 360 (6396) ◽  
pp. 1438-1442 ◽  
Author(s):  
Jianfeng Chen ◽  
Xing Gong ◽  
Jianyu Li ◽  
Yingkun Li ◽  
Jiguo Ma ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
High Activity ◽  
Asymmetric Catalysis ◽  
Carbonyl Group ◽  
Mannich Reaction ◽  
Primary Amine ◽  
Chiral Amines ◽  
Carbonyl Groups ◽  
Diphenylphosphinyl Imines

Chiral amines are widely used as catalysts in asymmetric synthesis to activate carbonyl groups for α-functionalization. Carbonyl catalysis reverses that strategy by using a carbonyl group to activate a primary amine. Inspired by biological carbonyl catalysis, which is exemplified by reactions of pyridoxal-dependent enzymes, we developed an N-quaternized pyridoxal catalyst for the asymmetric Mannich reaction of glycinate with aryl N-diphenylphosphinyl imines. The catalyst exhibits high activity and stereoselectivity, likely enabled by enzyme-like cooperative bifunctional activation of the substrates. Our work demonstrates the catalytic utility of the pyridoxal moiety in asymmetric catalysis.

Chiral primary amine thiourea promoted highly enantioselective Michael reactions of isobutylaldehyde with maleimides

Tetrahedron ◽  
2010 ◽  
Vol 66 (46) ◽  
pp. 8928-8932 ◽  
Author(s):  
Jian-Fei Bai ◽  
Lin Peng ◽  
Liang-liang Wang ◽  
Li-Xin Wang ◽  
Xiao-Ying Xu
Keyword(s):  
Primary Amine ◽  
Michael Reactions

scholarly journals Catalytic asymmetric formal synthesis of beraprost

2015 ◽  
Vol 11 ◽  
pp. 2654-2660 ◽  
Author(s):  
Yusuke Kobayashi ◽  
Ryuta Kuramoto ◽  
Yoshiji Takemoto
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Reaction ◽  
Subsequent Reduction ◽  
Formal Synthesis ◽  
Michael Adduct ◽  
Catalytic Asymmetric Synthesis ◽  
Weinreb Amide ◽  
Tricyclic Core ◽  
Catalytic Asymmetric

The first catalytic asymmetric synthesis of the key intermediate for beraprost has been achieved through an enantioselective intramolecular oxa-Michael reaction of an α,β-unsaturated amide mediated by a newly developed benzothiadiazine catalyst. The Weinreb amide moiety and bromo substituent of the Michael adduct were utilized for the C–C bond formations to construct the scaffold. All four contiguous stereocenters of the tricyclic core were controlled via Rh-catalyzed stereoselective C–H insertion and the subsequent reduction from the convex face.

scholarly journals Asymmetric Synthesis of Tertiary α -Hydroxyketones by Enantioselective Decarboxylative Chlorination and Subsequent Nucleophilic Substitution

Molecules ◽  
2020 ◽  
Vol 25 (17) ◽  
pp. 3902
Author(s):  
Mei Kee Kam ◽  
Akira Sugiyama ◽  
Ryouta Kawanishi ◽  
Kazutaka Shibatomi
Keyword(s):  
Asymmetric Synthesis ◽  
Nucleophilic Substitution ◽  
Primary Amine ◽  
Tetrabutylammonium Hydroxide ◽  
Tertiary Alcohols ◽  
Tertiary Carbon ◽  
Chiral Tertiary Alcohols

Chiral tertiary α-hydroxyketones were synthesized with high enantiopurity by asymmetric decarboxylative chlorination and subsequent nucleophilic substitution. We recently reported the asymmetric decarboxylative chlorination of β-ketocarboxylic acids in the presence of a chiral primary amine catalyst to obtain α-chloroketones with high enantiopurity. Here, we found that nucleophilic substitution of the resulting α-chloroketones with tetrabutylammonium hydroxide yielded the corresponding α-hydroxyketones without loss of enantiopurity. The reaction proceeded smoothly even at a tertiary carbon. The proposed method would be useful for the preparation of chiral tertiary alcohols.

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