scholarly journals Unprecedented copper-catalyzed asymmetric conjugate addition of organometallic reagents to α,β-unsaturated lactams

2004 ◽  
pp. 1244-1245 ◽  
Author(s):  
Mauro Pineschi ◽  
Federica Del Moro ◽  
Francesca Gini ◽  
Adriaan J. Minnaard ◽  
Ben L. Feringa
Keyword(s):  
Conjugate Addition ◽  
Organometallic Reagents

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.

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

Copper-Catalyzed Enantioselective Conjugate Addition to α,β-Unsaturated Aldehydes with Various Organometallic Reagents

Synthesis ◽  
2016 ◽  
Vol 48 (19) ◽  
pp. 3301-3308 ◽  
Author(s):  
Sylvie Goncalves-Contal ◽  
Ludovic Gremaud ◽  
Laëtitia Palais ◽  
Lucille Babel ◽  
Alexandre Alexakis
Keyword(s):  
Bond Formation ◽  
Conjugate Addition ◽  
Chiral Ligands ◽  
Grignard Reagents ◽  
Important Class ◽  
Reaction Conditions ◽  
Organometallic Reagents ◽  
Unsaturated Aldehydes

β-Substituted aldehydes constitute a very important class of compounds found in nature. Synthesis of this motif can be envisioned by C–C bond formation on enals. For this purpose, we report herein the development of enantioselective copper-catalyzed conjugate addition of various organometallic reagents to α,β-unsaturated aldehydes with (R)-H8BINAP, (R)-TolBINAP, and (R)-SEGPHOS as chiral ligands. Three sets of conditions were successfully developed and several enals were used. Reactivity and regio- and enantioselectivities were strongly dependent on reaction conditions and substrates. Good to excellent regio- and enantioselectivities were obtained with zinc reagents R2Zn and aluminum reagents R3Al. However, the asymmetric conjugate addition of Grignard reagents afforded only moderate to good regio- and enantioselectivities.

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