A visible-light-activated rhodium complex in enantioselective conjugate addition of α-amino radicals with Michael acceptors

2017 ◽  
Vol 53 (54) ◽  
pp. 7665-7668 ◽  
Author(s):  
Shao-Xia Lin ◽  
Gui-Jun Sun ◽  
Qiang Kang
Keyword(s):  
Visible Light ◽  
Conjugate Addition ◽  
Rhodium Complex ◽  
Michael Acceptors

An efficient enantioselective conjugate addition of photogenerated α-amino radicals to Michael acceptors catalyzed by a single and newly prepared chiral-at-metal rhodium complex was established.

scholarly journals Silyl-mediated photoredox-catalyzed Giese reaction: addition of non-activated alkyl bromides

2018 ◽  
Vol 9 (32) ◽  
pp. 6639-6646 ◽  
Author(s):  
Abdellatif ElMarrouni ◽  
Casey B. Ritts ◽  
Jaume Balsells
Keyword(s):  
Visible Light ◽  
Hdac Inhibitor ◽  
Addition Reaction ◽  
Conjugate Addition ◽  
Photoredox Catalysis ◽  
Unsaturated Esters ◽  
Alkyl Bromides ◽  
Michael Acceptors

The development of a conjugate addition reaction of non-activated alkyl bromides to Michael acceptors under visible-light photoredox catalysis is disclosed. A diverse set of alkyl bromides was successfully added to α,β-unsaturated esters and amides. This transformation allowed access to a key intermediate of Vorinostat®, an HDAC inhibitor used to fight cancer and HIV.

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.

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.

Conjugate addition from the excited state

2018 ◽  
Vol 54 (78) ◽  
pp. 11021-11024 ◽  
Author(s):  
Akila Iyer ◽  
Sapna Ahuja ◽  
Steffen Jockusch ◽  
Angel Ugrinov ◽  
Jayaraman Sivaguru
Keyword(s):  
Excited State ◽  
Visible Light ◽  
Conjugate Addition ◽  
Metal Free

Conjugate addition occurs efficiently from excited hydrazide based acrylanilides under both UV and metal free visible light irradiations.

Exploration of a Chiral Cobalt Catalyst for Visible‐Light‐Induced Enantioselective Radical Conjugate Addition

2019 ◽  
Vol 131 (38) ◽  
pp. 13509-13513 ◽  
Author(s):  
Kai Zhang ◽  
Liang‐Qiu Lu ◽  
Yue Jia ◽  
Ying Wang ◽  
Fu‐Dong Lu ◽  
...  
Keyword(s):  
Visible Light ◽  
Cobalt Catalyst ◽  
Conjugate Addition

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
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