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.

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.

Direct organocatalytic asymmetric Michael reaction of fluorine hemiaminal-type nucleophile to 4-nitro-5-styrylisoxazoles

2020 ◽  
Vol 7 (11) ◽  
pp. 1343-1348
Author(s):  
Luyao Li ◽  
Bo Zhu ◽  
Huihui Fan ◽  
Zhiyong Jiang ◽  
Junbiao Chang
Keyword(s):  
Michael Addition ◽  
Michael Reaction ◽  
Addition Reaction ◽  
Michael Addition Reaction ◽  
Asymmetric Michael Addition ◽  
Asymmetric Michael Reaction ◽  
First Time

Herein, we report a chiral bifunctional thiourea catalyzed asymmetric Michael addition reaction between 2-(trifluoromethyl)oxazol-5(2H)-one as a direct C-2-position nucleophile to 4-nitro-5-styrylisoxazoles for the first time.

Organocatalytic asymmetric Michael addition of 1-acetylcyclohexene and 1-acetylcyclopentene to nitroolefins

2015 ◽  
Vol 13 (25) ◽  
pp. 7076-7083 ◽  
Author(s):  
Utpal Nath ◽  
Ankush Banerjee ◽  
Bidhan Ghosh ◽  
Subhas Chandra Pan
Keyword(s):  
Michael Addition ◽  
Michael Reaction ◽  
Primary Amines ◽  
Asymmetric Michael Addition ◽  
Asymmetric Michael Reaction

The first organocatalytic asymmetric Michael reaction between α-branched enones namely 1-acetylcyclohexene, 1-acetylcyclopentene and 1-acetylcyclobutene with nitroolefins has been developed using primary amines as catalysts.

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 The synthesis of chiral β-naphthyl-β-sulfanyl ketones via enantioselective sulfa-Michael reaction in the presence of a bifunctional cinchona/sulfonamide organocatalyst

2021 ◽  
Vol 17 ◽  
pp. 494-503
Author(s):  
Deniz Tözendemir ◽  
Cihangir Tanyeli
Keyword(s):  
Michael Addition ◽  
Michael Reaction ◽  
Cinchona Alkaloid ◽  
Catalyst Loading ◽  
Asymmetric Transformations ◽  
Chalcone Derivatives ◽  
Mild Conditions ◽  
Michael Adducts

Cinchona alkaloid-derived organocatalysts are widely employed in various asymmetric transformations, yielding products with high enantiopurity. In this respect, a bifunctional quinine-derived sulfonamide organocatalyst was developed to catalyze the asymmetric sulfa-Michael reaction of naphthalene-1-thiol with trans-chalcone derivatives. The target sulfa-Michael adducts were obtained with up to 96% ee under mild conditions and with a low (1 mol %) catalyst loading. Selected enantiomerically enriched sulfa-Michael addition products were subjected to oxidation to obtain the corresponding sulfones.

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