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.

scholarly journals Synthesis of non-racemic 4-nitro-2-sulfonylbutan-1-ones via Ni(II)-catalyzed asymmetric Michael reaction of β-ketosulfones

2019 ◽  
Vol 15 ◽  
pp. 1289-1297 ◽  
Author(s):  
Alexander N Reznikov ◽  
Anastasiya E Sibiryakova ◽  
Marat R Baimuratov ◽  
Eugene V Golovin ◽  
Victor B Rybakov ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Bioactive Compounds ◽  
Michael Addition ◽  
Michael Reaction ◽  
High Yield ◽  
Michael Adducts ◽  
Significant Rate ◽  
Asymmetric Michael Addition ◽  
Stereogenic Centers ◽  
Asymmetric Michael Reaction

Functionally substituted sulfones with stereogenic centers are valuable reagents in organic synthesis and key motifs in some bioactive compounds. The asymmetric Michael addition of β-ketosulfones to conjugated nitroalkenes in the presence of Ni(II) complexes with various chiral vicinal diamines was studied. This reaction provides convenient access to non-racemic 4-nitro-2-sulfonylbutan-1-ones with two stereocenters with high yield and excellent enantioselectivity (up to 99%). It has been established that the catalytic Michael reaction itself was carried out with high diastereoselectivity, but the Michael adducts may epimerize at the C-2 position at a significant rate. Conditions for the preparation of individual diastereomers were found.

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

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.

scholarly journals Efficient Asymmetric Synthesis of Prostaglandin E1

2007 ◽  
Vol 62 (4) ◽  
pp. 556-560 ◽  
Author(s):  
Jae-Chul Jung ◽  
Oee-Sook Park
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Addition ◽  
Prostaglandin E1 ◽  
Simple Synthesis ◽  
High Yield ◽  
Prostaglandin E ◽  
Magnesium Bromide ◽  
One Pot ◽  
Asymmetric Michael Addition ◽  
Key Steps

A simple synthesis of prostaglandin E1 (PGE1) is described. The key steps are an asymmetric Michael addition to establish the desired (R)-configurations at C8 and C12 of the 2- (trimethylsilyl)ethoxymethyl- (SEM) protected PGE1 and its one-pot deprotection with magnesium bromide in high yield. This method is potentially useful for the preparation of other modified prostaglandins.

scholarly journals Primary-tertiary diamine-catalyzed Michael addition of ketones to isatylidenemalononitrile derivatives

2014 ◽  
Vol 10 ◽  
pp. 929-935 ◽  
Author(s):  
Akshay Kumar ◽  
Swapandeep Singh Chimni
Keyword(s):  
Amino Acids ◽  
Sodium Borohydride ◽  
Michael Addition ◽  
High Yield ◽  
Michael Adduct ◽  
Michael Adducts ◽  
Primary Amino ◽  
The Michael Addition

Simple primary-tertiary diamines easily derived from natural primary amino acids were used to catalyze the Michael addition of ketones with isatylidenemalononitrile derivatives. Diamine 1a in combination with D-CSA as an additive provided Michael adducts in high yield (up to 94%) and excellent enantioselectivity (up to 99%). The catalyst 1a was successfully used to catalyze the three-component version of the reaction by a domino Knoevenagel–Michael sequence. The Michael adduct 4a was transformed into spirooxindole 6 by a reduction with sodium borohydride in a highly enantioselective manner.

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