Construction of five-membered rings by Michael addition-radical cyclization

1987 ◽  
Vol 52 (22) ◽  
pp. 4943-4953 ◽  
Author(s):  
Derrick L. J. Clive ◽  
Taryn L. B. Boivin ◽  
A. Gaetan Angoh
Keyword(s):  
Michael Addition ◽  
Radical Cyclization

Highly Functionalized Cyclopentane Derivatives by Tandem Michael Addition/Radical Cyclization/Oxygenation Reactions

2015 ◽  
Vol 21 (27) ◽  
pp. 9877-9888 ◽  
Author(s):  
Martin Holan ◽  
Radek Pohl ◽  
Ivana Císařová ◽  
Blanka Klepetářová ◽  
Peter G. Jones ◽  
...  
Keyword(s):  
Michael Addition ◽  
Radical Cyclization

Formation of cis-fused cyclopentanoids by Michael addition and radical cyclization

1989 ◽  
Vol 54 (8) ◽  
pp. 1997-2003 ◽  
Author(s):  
Derrick L. J. Clive ◽  
Taryn L. B. Boivin
Keyword(s):  
Michael Addition ◽  
Radical Cyclization

Aerobic copper-catalyzed oxidative [6C+1C] annulation: an efficient route to seven-membered carbocycles

2014 ◽  
Vol 50 (63) ◽  
pp. 8764-8767 ◽  
Author(s):  
Xiao Liu ◽  
Lingjuan Zhang ◽  
Xianxiu Xu ◽  
Shan Wang ◽  
Ling Pan ◽  
...  
Keyword(s):  
Michael Addition ◽  
Oxidation Reaction ◽  
Ethyl Cyanoacetate ◽  
Radical Cyclization ◽  
Diastereoselective Synthesis ◽  
Ketene Dithioacetals ◽  
Efficient Route

A copper-catalyzed aerobic tandem Michael addition–intramolecular radical cyclization–benzyl C(sp3)–H bond oxidation reaction of dicinnamoyl ketene dithioacetals and ethyl cyanoacetate was developed for the diastereoselective synthesis of seven-membered carbocycles.

One-Pot Michael Addition/Radical Cyclization Reaction of N-Acryloyl Indoles

Synlett ◽  
2017 ◽  
Vol 28 (20) ◽  
pp. 2859-2864 ◽  
Author(s):  
Lauren Irwin ◽  
Michael Kerr
Keyword(s):  
Michael Addition ◽  
Radical Cyclization ◽  
Cyclization Reaction ◽  
One Pot

From N-acryloyl indoles, ten examples of 1,2-annulated ­indole products were generated in a one-pot procedure via a Michael addition and radical cyclization mediated by Mn(OAc)3.

ChemInform Abstract: Construction of Five-Membered Rings by Michael Addition-Radical Cyclization.

ChemInform ◽  
1988 ◽  
Vol 19 (15) ◽  
Author(s):  
D. L. J. CLIVE ◽  
T. L. B. BOIVIN ◽  
A. G. ANGOH
Keyword(s):  
Michael Addition ◽  
Radical Cyclization

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

2000 ◽  
Vol 24 (4) ◽  
pp. 467-476 ◽  
Author(s):  
Sabine Vollenweider ◽  
Hans Weber ◽  
Stephanie Stolz ◽  
Aurore Chetelat ◽  
Edward E. Farmer
Keyword(s):  
Fatty Acid ◽  
Michael Addition

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

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>

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

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.

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