Enantioselective Addition of Pyrazoles to Dienes

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

10.26434/chemrxiv.11830935.v1 ◽

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

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Chiral Oxazaborolidines as Catalysts for the Enantioselective Addition of Diethylzinc to Aldehydes

10.21236/ada210543 ◽

1989 ◽

Author(s):

N. N. Joshi ◽

M. Srebnik ◽

H. C. Brown

Keyword(s):

Enantioselective Addition

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

Organic & Biomolecular Chemistry ◽

10.1039/c9ob01338e ◽

2019 ◽

Vol 17 (31) ◽

pp. 7309-7314 ◽

Cited By ~ 2

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%).

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

Organic & Biomolecular Chemistry ◽

10.1039/d1ob00249j ◽

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...

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