ChemInform Abstract: Copper-Catalyzed Asymmetric Conjugate Addition of Organometallic Reagents to Extended Michael Acceptors

ChemInform ◽  
2016 ◽  
Vol 47 (12) ◽  
pp. no-no
Author(s):  
Thibault E. Schmid ◽  
Sammy Drissi-Amraoui ◽  
Christophe Crevisy ◽  
Olivier Basle ◽  
Marc Mauduit
Keyword(s):  
Conjugate Addition ◽  
Organometallic Reagents ◽  
Michael Acceptors

scholarly journals Copper-catalyzed enantioselective conjugate addition of organometallic reagents to challenging Michael acceptors

2020 ◽  
Vol 16 ◽  
pp. 212-232 ◽  
Author(s):  
Delphine Pichon ◽  
Jennifer Morvan ◽  
Christophe Crévisy ◽  
Marc Mauduit
Keyword(s):  
Natural Products ◽  
Conjugate Addition ◽  
Catalytic Transformation ◽  
Chiral Molecules ◽  
Catalytic Systems ◽  
Organometallic Reagents ◽  
Recent Advances ◽  
Wide Range ◽  
Michael Acceptors

The copper-catalyzed enantioselective conjugate addition (ECA) of organometallic nucleophiles to electron-deficient alkenes (Michael acceptors) represents an efficient and attractive methodology for providing a wide range of relevant chiral molecules. In order to increase the attractiveness of this useful catalytic transformation, some Michael acceptors bearing challenging electron-deficient functions (i.e., aldehydes, thioesters, acylimidazoles, N-acyloxazolidinones, N-acylpyrrolidinones, amides, N-acylpyrroles) were recently investigated. Remarkably, only a few chiral copper-based catalytic systems have successfully achieved the conjugate addition of different organometallic reagents to these challenging Michael acceptors, with excellent regio- and enantioselectivity. Furthermore, thanks to their easy derivatization, the resulting chiral conjugated products could be converted into various natural products. The aim of this tutorial review is to summarize recent advances accomplished in this stimulating field.

scholarly journals Copper-catalyzed asymmetric conjugate addition of organometallic reagents to extended Michael acceptors

2015 ◽  
Vol 11 ◽  
pp. 2418-2434 ◽  
Author(s):  
Thibault E Schmid ◽  
Sammy Drissi-Amraoui ◽  
Christophe Crévisy ◽  
Olivier Baslé ◽  
Marc Mauduit
Keyword(s):  
Conjugate Addition ◽  
Chiral Molecules ◽  
Straightforward Manner ◽  
Organometallic Reagents ◽  
Stereogenic Centers ◽  
Michael Acceptors ◽  
Sequential Generation

The copper-catalyzed asymmetric conjugate addition (ACA) of nucleophiles onto polyenic Michael acceptors represents an attractive and powerful methodology for the synthesis of relevant chiral molecules, as it enables in a straightforward manner the sequential generation of two or more stereogenic centers. In the last decade, various chiral copper-based catalysts were evaluated in combination with different nucleophiles and Michael acceptors, and have unambiguously demonstrated their usefulness in the control of the regio- and enantioselectivity of the addition. The aim of this review is to report recent breakthroughs achieved in this challenging field.

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

scholarly journals Photoredox radical conjugate addition of dithiane-2-carboxylate promoted by an iridium(iii) phenyl-tetrazole complex: a formal radical methylation of Michael acceptors

2017 ◽  
Vol 8 (2) ◽  
pp. 1613-1620 ◽  
Author(s):  
Andrea Gualandi ◽  
Elia Matteucci ◽  
Filippo Monti ◽  
Andrea Baschieri ◽  
Nicola Armaroli ◽  
...  
Keyword(s):  
Michael Reaction ◽  
Conjugate Addition ◽  
Michael Acceptors

An iridium(iii) phenyl-tetrazole complex is a versatile catalyst for a new photocatalytic Michael reaction.

Copper-Catalyzed Asymmetric Conjugate Addition of Dimethylzinc to Acyl-N -methylimidazole Michael Acceptors: Scope, Limitations and Iterative Reactions

2016 ◽  
Vol 358 (15) ◽  
pp. 2519-2540 ◽  
Author(s):  
Sammy Drissi-Amraoui ◽  
Thibault E. Schmid ◽  
Jimmy Lauberteaux ◽  
Christophe Crévisy ◽  
Olivier Baslé ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Michael Acceptors

ChemInform Abstract: Copper-Catalyzed Asymmetric Conjugate Addition of Organometallic Reagents to Enones Using S,O-Ligands with a Xylofuranose Backbone.

ChemInform ◽  
2010 ◽  
Vol 31 (26) ◽  
pp. no-no
Author(s):  
Oscar Pamies ◽  
Gemma Net ◽  
Aurora Ruiz ◽  
Carmen Claver ◽  
Simon Woodward
Keyword(s):  
Conjugate Addition ◽  
Organometallic Reagents

Copper-Catalyzed Enantioselective Conjugate Addition of Organometallic Reagents to Acyclic Dienones

2007 ◽  
Vol 349 (11-12) ◽  
pp. 1931-1937 ◽  
Author(s):  
Radovan Šebesta ◽  
M. Gabriella Pizzuti ◽  
Adriaan J. Minnaard ◽  
Ben L. Feringa
Keyword(s):  
Conjugate Addition ◽  
Organometallic Reagents

Copper-Catalysed Asymmetric Conjugate Addition of Organometallic Reagents to Linear Enones

Tetrahedron ◽  
2000 ◽  
Vol 56 (18) ◽  
pp. 2847-2855 ◽  
Author(s):  
Simon M.W Bennett ◽  
Stephen M Brown ◽  
Anthony Cunningham ◽  
Michael R Dennis ◽  
James P Muxworthy ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Organometallic Reagents
Sign in / Sign up

Export Citation Format

Share Document