scholarly journals Trapping of chiral enolates generated by Lewis acid promoted conjugate addition of Grignard reagents to unreactive Michael acceptors by various electrophiles

2019 ◽  
Vol 55 (78) ◽  
pp. 11766-11769
Author(s):  
Denisa Vargová ◽  
Juana M. Pérez ◽  
Syuzanna R. Harutyunyan ◽  
Radovan Šebesta
Keyword(s):  
Carboxylic Acids ◽  
Lewis Acid ◽  
Conjugate Addition ◽  
Grignard Reagents ◽  
Michael Acceptors ◽  
Chiral Enolates

Chiral enolates generated by asymmetric Cu-catalyzed and Lewis acid promoted conjugate addition of Grignard reagents to unsaturated amides, alkenylheterocycles, and carboxylic acids are trapped with cations, activated alkenes, or bromine.

scholarly journals Lewis Acid Promoted Trapping of Chiral Aza-enolates

Synthesis ◽  
2019 ◽  
Vol 51 (05) ◽  
pp. 1253-1262
Author(s):  
Francesco Lanza ◽  
Juana Pérez ◽  
Ravindra Jumde ◽  
Syuzanna Harutyunyan
Keyword(s):  
Lewis Acid ◽  
Conjugate Addition ◽  
Conventional Wisdom ◽  
Grignard Reagents ◽  
One Pot ◽  
Michael Acceptor ◽  
Michael Acceptors ◽  
Reactivity Order

We present a study on sequential conjugate addition of ­Grignard reagents to alkenyl-heteroarenes followed by trapping of the resulting enolates, yielding moderate to good diastereoselectivities. Contrary to conventional wisdom, one-pot conjugate addition/trapping using two reactive Michael acceptors in combination with Grignard reagents can proceed via conjugate addition to the least reactive Michael acceptor. This unusual chemoselectivity is triggered by the presence of a Lewis acid, reverting the usual reactivity order of Michael acceptors.

Copper-Catalyzed Asymmetric Conjugate Addition of Dimethylzinc to Acyl-N-methylimidazole Michael Acceptors: a Powerful Synthetic Platform

2015 ◽  
Vol 127 (40) ◽  
pp. 11996-12000 ◽  
Author(s):  
Sammy Drissi-Amraoui ◽  
Marie S. T. Morin ◽  
Christophe Crévisy ◽  
Olivier Baslé ◽  
Renata Marcia de Figueiredo ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Michael Acceptors
Sign in / Sign up

Export Citation Format

Share Document