ChemInform Abstract: Bifunctional Iminophosphorane Catalyzed Enantioselective Sulfa-Michael Addition to Unactivated α-Substituted Acrylate Esters.

In addition to 4-acetyl-5-oxohexanoate esters (I), the expected product of the Michael addition of acetylacetone to acrylates, three other products (III, IV, V) have been isolated from this reaction. The amount of sodium alkoxide used as catalyst in the reaction largely determines the proportions of the products obtained. Some aspects of the chemistry of these compounds are discussed.

Download Full-text

Bifunctional Iminophosphorane Catalyzed Enantioselective Sulfa-Michael Addition to Unactivated α-Substituted Acrylate Esters

Journal of the American Chemical Society ◽

10.1021/jacs.5b10226 ◽

2015 ◽

Vol 137 (51) ◽

pp. 15992-15995 ◽

Cited By ~ 69

Author(s):

Alistair J. M. Farley ◽

Christopher Sandford ◽

Darren J. Dixon

Keyword(s):

Michael Addition ◽

Acrylate Esters

Download Full-text

Fatty acid ketodienes and fatty acid ketotrienes: Michael addition acceptors that accumulate in wounded and diseased Arabidopsis leaves

The Plant Journal ◽

10.1046/j.1365-313x.2000.00897.x ◽

2000 ◽

Vol 24 (4) ◽

pp. 467-476 ◽

Cited By ~ 127

Author(s):

Sabine Vollenweider ◽

Hans Weber ◽

Stephanie Stolz ◽

Aurore Chetelat ◽

Edward E. Farmer

Keyword(s):

Fatty Acid ◽

Michael Addition

Download Full-text

Computational studies on geopolymer catalyst for Michael addition reaction

10.1021/scimeetings.0c05563 ◽

2020 ◽

Author(s):

Uppari Naveena

Keyword(s):

Michael Addition ◽

Addition Reaction ◽

Computational Studies ◽

Michael Addition Reaction

Download Full-text

Ligand-Enabled γ-C(sp3)–H Olefination of Free Carboxylic Acids

10.26434/chemrxiv.11857857 ◽

2020 ◽

Author(s):

Kiron Kumar Ghosh ◽

Alexander Uttry ◽

Francesca Ghiringhelli ◽

Arup Mondal ◽

Manuel van Gemmeren

Keyword(s):

Reaction Mechanism ◽

Carboxylic Acids ◽

Michael Addition ◽

Kinetic Studies ◽

Wide Range ◽

Palladium Catalyzed

We report the ligand enabled C(sp3)–H activation/olefination of free carboxylic acids in the γ-position. Through an intramolecular Michael-addition, δ-lactones are obtained as products. Two distinct ligand classes are identified that enable the challenging palladium-catalyzed activation of free carboxylic acids in the γ-position. The developed protocol features a wide range of acid substrates and olefin reaction partners and is shown to be applicable on a preparatively useful scale. Insights into the underlying reaction mechanism obtained through kinetic studies are reported.<br>

Download Full-text

Cupin Variants as Macromolecular Ligand Library for Stereoselective Michael Addition of Nitroalkanes

10.26434/chemrxiv.11481834.v1 ◽

2019 ◽

Author(s):

Nobutaka Fujieda ◽

Miho Yuasa ◽

Yosuke Nishikawa ◽

Genji Kurisu ◽

Shinobu Itoh ◽

...

Keyword(s):

Michael Addition ◽

In Silico ◽

Addition Reaction ◽

Single Point ◽

Point Mutations ◽

Unsaturated Ketone ◽

Michael Addition Reaction ◽

Beta Barrel ◽

Cupin Superfamily ◽

Single Point Mutations

Cupin superfamily proteins (TM1459) work as a macromolecular ligand framework with a double-stranded beta-barrel structure ligating to a Cu ion through histidine side chains. Variegating the first coordination sphere of TM1459 revealed that H52A and H54A/H58A mutants effectively catalyzed the diastereo- and enantio-selective Michael addition reaction of nitroalkanes to an α,β-unsaturated ketone. Moreover, in silico substrate docking signified C106N and F104W single-point mutations, which inverted the diastereoselectivity of H52A and further improved the stereoselectivity of H54A/H58A, respectively.

Download Full-text

Enantioselective Michael Addition of Malonates to Enones

Current Organic Chemistry ◽

10.2174/1385272824666200316122221 ◽

2020 ◽

Vol 24 (7) ◽

pp. 746-773

Author(s):

Péter Bakó ◽

Tamás Nemcsok ◽

Zsolt Rapi ◽

György Keglevich

Keyword(s):

Michael Addition ◽

Activity Relationship ◽

Chalcone Derivatives ◽

Michael Additions ◽

Michael Reactions ◽

Structure Activity ◽

Cyclic Enones ◽

Michael Acceptors ◽

Relationship Of ◽

Enantioselective Catalysts

: Many catalysts were tested in asymmetric Michael additions in order to synthesize enantioenriched products. One of the most common reaction types among the Michael reactions is the conjugated addition of malonates to enones making it possible to investigate the structure–activity relationship of the catalysts. The most commonly used Michael acceptors are chalcone, substituted chalcones, chalcone derivatives, cyclic enones, while typical donors may be dimethyl, diethyl, dipropyl, diisopropyl, dibutyl, di-tert-butyl and dibenzyl malonates. This review summarizes the most important enantioselective catalysts applied in these types of reactions.

Download Full-text