scholarly journals Simple primary β-amino alcohols as organocatalysts for the asymmetric Michael addition of β-keto esters to nitroalkenes

RSC Advances ◽  
2021 ◽  
Vol 11 (1) ◽  
pp. 203-209
Author(s):  
Zubeda Begum ◽  
Haruka Sannabe ◽  
Chigusa Seki ◽  
Yuko Okuyama ◽  
Eunsang Kwon ◽  
...  
Keyword(s):  
Michael Addition ◽  
Amino Alcohols ◽  
Keto Esters ◽  
Michael Adducts ◽  
Asymmetric Michael Addition

Simple primary β-amino alcohols X act as an efficient organocatalysts in the asymmetric Michael addition of β-keto esters A with nitroalkenes B affording highly pure chiral Michael adducts C.

Sugar Based γ-Amino Alcohol Organocatalyst for Asymmetric Michael Addition of β-Keto Esters with Nitroolefins

Heterocycles ◽  
2019 ◽  
Vol 98 (11) ◽  
pp. 1536 ◽  
Author(s):  
Hiroto Nakano ◽  
Divakar Ganesan ◽  
Madhu Chennapuram ◽  
Zubeda Begum ◽  
Chigusa Seki ◽  
...  
Keyword(s):  
Michael Addition ◽  
Amino Alcohol ◽  
Keto Esters ◽  
Asymmetric Michael Addition

scholarly journals Amino Amide Organocatalysts for Asymmetric Michael Addition of β-Keto Esters with β-Nitroolefins

2019 ◽  
Vol 92 (3) ◽  
pp. 696-701 ◽  
Author(s):  
Isiaka Alade Owolabi ◽  
Madhu Chennapuram ◽  
Chigusa Seki ◽  
Yuko Okuyama ◽  
Eunsang Kwon ◽  
...  
Keyword(s):  
Michael Addition ◽  
Keto Esters ◽  
Asymmetric Michael Addition ◽  
Amino Amide

Novel ferrocene-based bifunctional amine–thioureas for asymmetric Michael addition of acetylacetone to nitroolefins

2015 ◽  
Vol 13 (17) ◽  
pp. 5054-5060 ◽  
Author(s):  
Xiaochen Ren ◽  
Chunyan He ◽  
Yingle Feng ◽  
Yonghai Chai ◽  
Wei Yao ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Efficient Method ◽  
Michael Addition ◽  
High Yield ◽  
Bifunctional Catalysts ◽  
Michael Adducts ◽  
Asymmetric Michael Addition ◽  
Multiple Hydrogen Bonding

An efficient method was developed to synthesize the ferrocene-based bifunctional amine–thioureas bearing multiple hydrogen-bonding donors. Asymmetric Michael addition of acetylacetone to nitroolefins catalyzed by these novel bifunctional catalysts affords the Michael adducts in high yield and moderate to excellent enantioselectivities.

Enantioselective Asymmetric Michael Addition of Cyclic Diketones to β,γ-Unsaturated α-Keto Esters

2012 ◽  
Vol 2012 (19) ◽  
pp. 3691-3696 ◽  
Author(s):  
Yi-Feng Wang ◽  
Ke Wang ◽  
Wei Zhang ◽  
Bin-Bin Zhang ◽  
Chi-Xiao Zhang ◽  
...  
Keyword(s):  
Michael Addition ◽  
Keto Esters ◽  
Asymmetric Michael Addition

Highly Enantioselective Michael Addition of Dithiomalonates to Nitroolefins Catalyzed by New Bifunctional Chiral Thioureas

Synthesis ◽  
2018 ◽  
Vol 50 (13) ◽  
pp. 2577-2586 ◽  
Author(s):  
Jia-Ni Yuan ◽  
Hui-Xia Liu ◽  
Qin-Qin Tian ◽  
Nan Ji ◽  
Kuo Shen ◽  
...  
Keyword(s):  
Michael Addition ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Michael Adducts ◽  
Asymmetric Michael Addition ◽  
High Yields

We report a highly efficient asymmetric Michael addition of dithiomalonates to trans-β-nitroolefins catalyzed by versatile cinchona-based bifunctional thioureas, which provides the corresponding adducts in high yields (up to 92%) and with excellent enantioselectivities (up to 99% ee) under mild conditions. Replacement of the catalyst with its pseudo-enantiomer gives the Michael adducts with opposite configuration in similar yields and enantioselectivities.

ChemInform Abstract: Enantioselective Asymmetric Michael Addition of Cyclic Diketones to β,γ-Unsaturated α-Keto Esters.

ChemInform ◽  
2012 ◽  
Vol 43 (48) ◽  
pp. no-no
Author(s):  
Yi-Feng Wang ◽  
Ke Wang ◽  
Wei Zhang ◽  
Bin-Bin Zhang ◽  
Chi-Xiao Zhang ◽  
...  
Keyword(s):  
Michael Addition ◽  
Keto Esters ◽  
Asymmetric Michael Addition

Highly Enantioselective Michael Addition of Cyclic Diketones to β,γ-Unsaturated α-Keto Esters Catalyzed by Squaramide Organocatalyst

Synthesis ◽  
2022 ◽  
Author(s):  
Zhi-Wei Ma ◽  
Chuan-Chuan Wang ◽  
Quan-Jian Lv ◽  
Xiao-Pei Chen ◽  
Ai-Qin Li ◽  
...  
Keyword(s):  
Michael Addition ◽  
Large Scale ◽  
Catalyst System ◽  
Catalyst Loading ◽  
Reaction Conditions ◽  
Keto Esters ◽  
Bicyclic Compounds ◽  
Asymmetric Michael Addition ◽  
High Yields ◽  
Low Catalyst Loading

AbstractA new tertiary amine-squaramide organocatalyst has been developed and applied to the asymmetric Michael addition of cyclic diketones to β,γ-unsaturated α-keto esters. The catalyst system performed well with a low catalyst loading of 1 mol% under mild reaction conditions. A series of synthetically and pharmaceutically useful chiral bicyclic compounds were obtained in high yields (up to 97%) with excellent enantioselectivities (up to 99 % ee). Furthermore, this catalytic system can be used efficiently in large-scale reactions with the yields and enantioselectivities being maintained.

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