New simple primary amine–thiourea organocatalysts and their application in asymmetric conjugate addition

2014 ◽  
Vol 55 (27) ◽  
pp. 3697-3700 ◽  
Author(s):  
Lu Yu ◽  
Pengfei Li
Keyword(s):  
Primary Amine ◽  
Conjugate Addition

The role of reversibility in the enantioselective conjugate addition of α,α-disubstituted aldehydes to nitro-olefins catalyzed by primary amine thioureas

2014 ◽  
Vol 4 (10) ◽  
pp. 3505-3509 ◽  
Author(s):  
Yining Ji ◽  
Donna G. Blackmond
Keyword(s):  
Primary Amine ◽  
Conjugate Addition ◽  
Mechanistic Insight

Identification of intermediates in the asymmetric conjugate addition of aldehdyes to nitro-olefins catalyzed by primary amine thioureas add mechanistic insight.

scholarly journals Organocatalytic Asymmetric Conjugate Addition of Aldehydes to Maleimides and Nitroalkenes in Deep Eutectic Solvents

Molecules ◽  
2019 ◽  
Vol 24 (22) ◽  
pp. 4058 ◽  
Author(s):  
Alejandro Torregrosa-Chinillach ◽  
Alba Sánchez-Laó ◽  
Elisa Santagostino ◽  
Rafael Chinchilla
Keyword(s):  
Primary Amine ◽  
Room Temperature ◽  
Deep Eutectic Solvents ◽  
Conjugate Addition ◽  
Reaction Media

A chiral primary amine-salicylamide is used as an organocatalyst for the enantioselective conjugate addition of α,α-disubstituted aldehydes to maleimides and nitroalkenes. The reactions are performed in deep eutectic solvents as reaction media at room temperature, leading to the corresponding adducts with enantioselectivities up to 88% (for maleimides) and 80% (for nitroalkenes). Catalyst and solvent can be recovered and reused.

ChemInform Abstract: A Simple Primary Amine Thiourea Catalyzed Highly Enantioselective Conjugate Addition of α,α-Disubstituted Aldehydes to Maleimides.

ChemInform ◽  
2010 ◽  
Vol 41 (49) ◽  
pp. no-no
Author(s):  
Fei Xue ◽  
Lu Liu ◽  
Shilei Zhang ◽  
Wenhu Duan ◽  
Wei Wang
Keyword(s):  
Primary Amine ◽  
Conjugate Addition

scholarly journals Enantioselective Michael Addition of Aldehydes to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide

Molecules ◽  
2018 ◽  
Vol 23 (12) ◽  
pp. 3299 ◽  
Author(s):  
Alejandro Torregrosa-Chinillach ◽  
Adrien Moragues ◽  
Haritz Pérez-Furundarena ◽  
Rafael Chinchilla ◽  
Enrique Gómez-Bengoa ◽  
...  
Keyword(s):  
Michael Addition ◽  
Primary Amine ◽  
Room Temperature ◽  
Theoretical Calculations ◽  
Conjugate Addition ◽  
High Yields

A primary amine-salicylamide derived from chiral trans-cyclohexane-1,2-diamine was used as an organocatalyst for the enantioselective conjugate addition of aldehydes, mainly α,α-disubstituted to N-substituted maleimides. The reaction was performed in toluene as a solvent at room temperature. The corresponding enantioenriched adducts were obtained with high yields and enantioselectivities up to 94%. Theoretical calculations were used to justify the stereoinduction.

Sign in / Sign up

Export Citation Format

Share Document