Activation of Vinyl Iodides for the Highly Enantioselective Addition to Aldehydes

2011 ◽  
Vol 50 (10) ◽  
pp. 2368-2370 ◽  
Author(s):  
Albert M. DeBerardinis ◽  
Mark Turlington ◽  
Lin Pu
Keyword(s):  
Enantioselective Addition ◽  
Vinyl Iodides

ChemInform Abstract: Activation of Vinyl Iodides for the Highly Enantioselective Addition to Aldehydes.

ChemInform ◽  
2011 ◽  
Vol 42 (26) ◽  
pp. no-no
Author(s):  
Albert M. DeBerardinis ◽  
Mark Turlington ◽  
Lin Pu
Keyword(s):  
Enantioselective Addition ◽  
Vinyl Iodides

Activation of Vinyl Iodides for the Highly Enantioselective Addition to Aldehydes

2011 ◽  
Vol 123 (10) ◽  
pp. 2416-2418 ◽  
Author(s):  
Albert M. DeBerardinis ◽  
Mark Turlington ◽  
Lin Pu
Keyword(s):  
Enantioselective Addition ◽  
Vinyl Iodides

Regio-, Stereo- and Enantioselective α-Addition of Carbonyl Nucleo-philes to Allenamides Catalyzed by a Synergistic Copper/Enamine System

2020 ◽  
Author(s):  
Rémi Blieck ◽  
Sebastien Lemouzy ◽  
Marc Taillefer ◽  
Florian Monnier
Keyword(s):  
Catalytic System ◽  
Secondary Amine ◽  
Primary Amine ◽  
Synergistic Catalysis ◽  
Enantioselective Addition ◽  
Amine Catalysts

A dual copper/enamine catalytic system is found to enable an intermolecular enantioselective α-addition of various carbonyl nucleophiles to allenamides. Secondary amine catalysts allowed the highly enantioselective addition of aldehydes, while using primary amine catalysts led to the enantioselective addition of ketoester nucleophiles. The process was found to be highly regio-, stereo- and enantio-selective and represented the first allene hydrofunctionalization using an synergistic catalysis involving copper

Stereospecific, Palladium-catalyzed C(sp3)–H Alkenylation and Alkynylation of a Proline Derivative Enabled by 8-Aminoquinoline as a Directing Group

2020 ◽  
Author(s):  
Aleksandra Balliu ◽  
Aaltje Roelofje Femmigje Strijker ◽  
Michael Oschmann ◽  
Monireh Pourghasemi Lati ◽  
Oscar Verho
Keyword(s):  
Carboxylic Acid ◽  
Building Blocks ◽  
Wide Range ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
High Yields ◽  
Vinyl Iodides ◽  
Initial Results

<p>In this preprint, we present our initial results concerning a stereospecific Pd-catalyzed protocol for the C3 alkenylation and alkynylation of a proline derivative carrying the well utilized 8‑aminoquinoline directing group. Efficient C–H alkenylation was achieved with a wide range of vinyl iodides bearing different aliphatic, aromatic and heteroaromatic substituents, to furnish the corresponding C3 alkenylated products in good to high yields. In addition, we were able show that this protocol can also be used to install an alkynyl group into the pyrrolidine scaffold, when a TIPS-protected alkynyl bromide was used as the reaction partner. Furthermore, two different methods for the removal of the 8-aminoquinoline auxiliary are reported, which can enable access to both <i>cis</i>- and <i>trans</i>-configured carboxylic acid building blocks from the C–H alkenylation products.</p>

Highly enantioselective addition of sulfur-containing heterocycles to isatin-derived ketimines

2019 ◽  
Vol 17 (31) ◽  
pp. 7309-7314 ◽  
Author(s):  
Michael Franc ◽  
Michal Urban ◽  
Ivana Císařová ◽  
Jan Veselý
Keyword(s):  
Heterocyclic Compounds ◽  
Stereoselective Addition ◽  
Enantioselective Addition ◽  
Sulfur Containing

In this study, we report a highly stereoselective addition of sulfur-containing heterocyclic compounds to isatin-derived ketimines efficiently catalyzed by cinchonidine-derived bifunctional tertiary aminothiourea (1 mol%).

Dimethylzinc-mediated enantioselective addition of terminal alkynes to 1,2-diketones using perhydro-1,3-benzoxazines as ligands

2021 ◽  
Author(s):  
Elena Prieto ◽  
Rebeca Infante ◽  
Javier Nieto ◽  
Celia Andres
Keyword(s):  
Chiral Ligand ◽  
Terminal Alkynes ◽  
Conformationally Restricted ◽  
Enantioselective Addition

A conformationally restricted perhydro-1,3-benzoxazine derived from (-)-8-aminomenthol behaves as a good chiral ligand in the dimethylzinc-mediated enantioselective monoaddition of aromatic and aliphatic terminal alkynes to 1,2-diketones. The corresponding α-hydroxyketones were...

A Convenient Synthesis of Piperidine-Based β-Amino Alcohols from L-Phe and Highly Enantioselective Addition of Diethyl Zinc to Aldehydes.

ChemInform ◽  
2003 ◽  
Vol 34 (28) ◽  
Author(s):  
Chao-shan Da ◽  
Zhi-jian Han ◽  
Ming Ni ◽  
Fan Yang ◽  
Da-xue Liu ◽  
...  
Keyword(s):  
Amino Alcohols ◽  
Diethyl Zinc ◽  
Convenient Synthesis ◽  
Enantioselective Addition
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