Copper-Catalyzed Hydroarylation of Internal Alkynes: Highly Regio- and Diastereoselective Synthesis of 1,1-Diaryl, Trisubstituted Olefins

ACS Catalysis ◽  
2017 ◽  
Vol 7 (9) ◽  
pp. 6220-6224 ◽  
Author(s):  
Gregory D. Kortman ◽  
Kami L. Hull
Keyword(s):  
Diastereoselective Synthesis ◽  
Internal Alkynes ◽  
Trisubstituted Olefins

scholarly journals Diastereoselective synthesis of trisubstituted olefins using a silicon-tether ring-closing metathesis strategy

2020 ◽  
Vol 18 (12) ◽  
pp. 2297-2306
Author(s):  
Stéphane Wittmann ◽  
Alexander F. Tiniakos ◽  
Joëlle Prunet
Keyword(s):  
Diastereoselective Synthesis ◽  
Ring Closing Metathesis ◽  
Trisubstituted Olefins ◽  
Trisubstituted Alkenes

We report an efficient and diastereoselective synthesis of E- and Z-trisubstituted alkenes by a silicon-tether ring-closing metathesis strategy.

scholarly journals Palladium-Catalyzed Asymmetric Hydrophosphination of Internal Alkynes: Highly Regio- and Stereoselective Construction of Axially Chiral Phosphines

2021 ◽  
Author(s):  
Danqing Ji ◽  
Jierui Jing ◽  
Yi Wang ◽  
Zisong Qi ◽  
Fen Wang ◽  
...  
Keyword(s):  
Axial Chirality ◽  
Axially Chiral ◽  
Internal Alkynes ◽  
Trisubstituted Olefins ◽  
Palladium Catalyzed ◽  
Chiral Phosphines ◽  
Kinetic Transformation ◽  
Secondary Phosphines

Palladium-catalyzed unprecedented atroposelective hydrophosphination of internal alkynes has been realized using diarylphosphines, affording C-N axially chiral trisubstituted olefins (vinylphosphines) in excellent regioselectiviry, (E)-selectivity, and enantioselectivity. The axial chirality was established via integration of hydrophosphination and dynamic kinetic transformation of the alkynes, with both symmetrical and nonsymmetrical secondary phosphines being applicable. In the latter case, additional P-central chirality has been constructed in good diastereoselectivity.

Synthesis of trisubstituted olefins via nickel-catalyzed decarboxylative hydroalkylation of internal alkynes

Tetrahedron ◽  
2018 ◽  
Vol 74 (49) ◽  
pp. 6979-6984 ◽  
Author(s):  
Xiao-Yu Lu ◽  
Jing-Song Li ◽  
Mei-Lan Hong ◽  
Jin-Yu Wang ◽  
Wen-Jing Ma
Keyword(s):  
Internal Alkynes ◽  
Trisubstituted Olefins

Ruthenium(II)-Catalyzed Intermolecular Cyclo(co)trimerization of 3-Halopropiolamides with Internal Alkynes

2018 ◽  
Author(s):  
Anthony P. Silvestri ◽  
James S. Oakdale
Keyword(s):  
Ambient Temperature ◽  
Internal Alkynes

<div>A highly chemo- and regioselective cyclo(co)trimerization between 3-halopropiolamides and symmetrical internal alkynes is reported. The reaction is catalyzed by Ru(II)-complexes and proceeds at ambient temperature in ethanol to deliver fully substituted dihalogenated isophthalamides. 1,4-Butynediol was found to undergo spontaneous lactonization with halopropiolamides after trimerization to provide 5,7-dihalo-phthalide products.</div>

Naturally Occurring Organic Acid-catalyzed Facile Diastereoselective Synthesis of Biologically Active (E)-3-(arylimino)indolin-2-one Derivatives in Water at Room Temperature

2019 ◽  
Vol 23 (16) ◽  
pp. 1778-1788 ◽  
Author(s):  
Gurpreet Kaur ◽  
Arvind Singh ◽  
Kiran Bala ◽  
Mamta Devi ◽  
Anjana Kumari ◽  
...  
Keyword(s):  
Room Temperature ◽  
Biologically Active ◽  
Environmentally Benign ◽  
Diastereoselective Synthesis ◽  
Substituted Anilines ◽  
Reaction Conditions ◽  
Naturally Occurring ◽  
Acid Catalyzed ◽  
Reaction Media ◽  
Column Chromatographic

A simple, straightforward and efficient method has been developed for the synthesis of (E)-3-(arylimino)indolin-2-one derivatives and (E)-2-((4-methoxyphenyl)imino)- acenaphthylen-1(2H)-one. The synthesis of these biologically-significant scaffolds was achieved from the reactions of various substituted anilines and isatins or acenaphthaquinone, respectively, using commercially available, environmentally benign and naturally occurring organic acids such as mandelic acid or itaconic acid as catalyst in aqueous medium at room temperature. Mild reaction conditions, energy efficiency, good to excellent yields, environmentally benign conditions, easy isolation of products, no need of column chromatographic separation and the reusability of reaction media are some of the significant features of the present protocol.

Diastereoselective Synthesis of Novel Optically Active Five Membered O- and N-heterocyclic Compounds

2012 ◽  
Vol 9 (2) ◽  
pp. 81-88 ◽  
Author(s):  
Ervin Kovacs ◽  
Ferenc Farkas ◽  
Angelika Thurner ◽  
Aron Szollosy ◽  
Ferenc Faigl
Keyword(s):  
Heterocyclic Compounds ◽  
Optically Active ◽  
Diastereoselective Synthesis
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