Study on Organocatalytic Asymmetric Michael Addition in Aqueous Media by a Hydrogen-Bonding Catalyst and Application for Inhibitors of GABAB Receptor

Catalysts based on (R, R)-1,2-diphenylethylenediamine are, as chiral organic catalysts, applied to the asymmetric Michael addition to α, β-unsaturated nitroalkenes under neutral conditions. The role of an aqueous medium for organic catalytic activity can be reversed concerning hydrophilic-hydrophobic function depending on the reaction conditions. In this study, to provide an environmentally friendly system, the thiourea-based catalyst substituted with 3,5-(CF3)2-Ph was used in water solvents. The hydrophobic effect of the substituent provided fast reaction, high chemical yield, and mirror-image selectivity. This reaction allowed the preparation of GABAB agonists in an optically pure manner. Additionally, GABA (γ-aminobutyric acid) analogs such as baclofen and phenibut were synthesized as R-type S-type with high optical purity.

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

ChemInform ◽

10.1002/chin.201234019 ◽

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

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The carbamate esters as organocatalysts in asymmetric Michael addition reactions in aqueous media: when pyrrolidine backbone surpasses 1,2-diaminocyclohexane

ARKIVOC ◽

10.24820/ark.5550190.p010.692 ◽

2018 ◽

Vol 2018 (7) ◽

pp. 320-331 ◽

Cited By ~ 3

Author(s):

Anirban Mondal ◽

Kartick C. Bhowmick

Keyword(s):

Michael Addition ◽

Aqueous Media ◽

Addition Reactions ◽

Asymmetric Michael Addition

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

Organic & Biomolecular Chemistry ◽

10.1039/c5ob00298b ◽

2015 ◽

Vol 13 (17) ◽

pp. 5054-5060 ◽

Cited By ~ 14

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.

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