Chiral amine-thioureas bearing multiple hydrogen bonding donors: highly efficient organocatalysts for asymmetric Michael addition of acetylacetone to nitroolefins

2008 ◽  
pp. 1431 ◽  
Author(s):  
Chun-Jiang Wang ◽  
Zhi-Hai Zhang ◽  
Xiu-Qin Dong ◽  
Xiao-Jun Wu
Keyword(s):  
Hydrogen Bonding ◽  
Michael Addition ◽  
Chiral Amine ◽  
Highly Efficient ◽  
Asymmetric Michael Addition ◽  
Multiple Hydrogen Bonding

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.

ChemInform Abstract: Fast, Solvent-Free and Hydrogen-Bonding-Mediated Asymmetric Michael Addition in a Ball Mill.

ChemInform ◽  
2012 ◽  
Vol 43 (34) ◽  
pp. no-no
Author(s):  
Yi-Feng Wang ◽  
Ru-Xiang Chen ◽  
Ke Wang ◽  
Bin-Bin Zhang ◽  
Zhao-Bo Li ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Michael Addition ◽  
Ball Mill ◽  
Solvent Free ◽  
Asymmetric Michael Addition

ChemInform Abstract: Highly Efficient Amine Organocatalysts Based on Bispidine for the Asymmetric Michael Addition of Ketones to Nitroolefins.

ChemInform ◽  
2009 ◽  
Vol 40 (2) ◽  
Author(s):  
Zhigang Yang ◽  
Jie Liu ◽  
Xiaohua Liu ◽  
Zhen Wang ◽  
Xiaoming Feng ◽  
...  
Keyword(s):  
Michael Addition ◽  
Highly Efficient ◽  
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.

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