Chiral Propargyl Alcohols via the Enantioselective Addition of Terminal Di- and Triynes to Aldehydes

2011 ◽  
Vol 76 (16) ◽  
pp. 6574-6583 ◽  
Author(s):  
Erin R. Graham ◽  
Rik R. Tykwinski
Keyword(s):  
Enantioselective Addition ◽  
Propargyl Alcohols

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

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...

Visible-light-induced remote C(sp3)-H sulfonylvinylation: assembly of cyanoalkylated vinyl sulfones

2021 ◽  
Author(s):  
Ping Bao ◽  
Feiyan Yu ◽  
Fu-Sheng He ◽  
Zhimei Tang ◽  
Wei-Ping Deng ◽  
...  
Keyword(s):  
Visible Light ◽  
Rapid Access ◽  
Three Component Reaction ◽  
Propargyl Alcohols

A photoinduced sulfonylvinylation of unactivated C(sp3)-H bond through a three-component reaction of propargyl alcohols, potassium metabisulfite and cycloketone oxime esters is developed. This approach enables rapid access to cyanoalkylated vinyl...

Ru(II)-catalyzed Allenylation and Sequential Annulation of N-Tosylbenzamides with Propargyl Alcohols

2021 ◽  
Author(s):  
Chandra MR Volla ◽  
Shreemoyee Kumar ◽  
Akshay Murali Nair
Keyword(s):  
Propargyl Alcohols

We hereby report a Ru(II)-catalyzed C(sp2)-H allenylation of N-tosylbenzamides to access multi-substituted allenylamides. Furthermore, the allenylamides were converted to the corresponding isoquinolone derivatives via base mediated annulation. The current protocol...

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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