Alexandre Brethome
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[ASAP] Functional Group Transposition: A Palladium-Catalyzed Metathesis of Ar–X s-Bonds and Acid Chloride Synthesis
Iridium-Catalyzed Intramolecular Asymmetric Allylic Dearomatization Reaction of Benzoxazoles, Benzothiazoles, and Benzimidazoles
Alexandre BrethomePhosphoramidite
Abstract
An iridium-catalyzed intramolecular asymmetric allylic dearomatization reaction of benzoxazoles, benzothiazoles, and benzimidazoles was developed. The reaction was found to be compatible with a wide range of five-membered-ring electron-deficient heteroaromatic compounds and furnished the corresponding dearomatized heterocycles in high yield with excellent enantioselectivity.
Break up the party: A wide range of electron-deficient nitrogen-containing aromatic compounds with an allylic carbonate side chain underwent intramolecular asymmetric allylic dearomatization in the presence of an iridium catalyst with the chiral ligand Me-THQphos (see scheme). The corresponding dearomatized heterocycles were obtained in high yield with excellent enantioselectivity.
Regio- and Enantioselective Rhodium-Catalyzed Addition of 1,3-Diketones to Allenes: Construction of Asymmetric Tertiary and Quaternary All Carbon Centers
Alexandre BrethomePhosphoramidite ligands
Abstract
An unprecedented highly regio- and enantioselective rhodium-catalyzed addition of 1,3-diketones to terminal and 1,1-disubstituted allenes furnishing asymmetric tertiary and quaternary all-carbon centers is reported. By applying a RhI/phosphoramidite/TFA catalytic system under mild conditions, the desired chiral branched α-allylated 1,3-diketones could be obtained in good to excellent yields, with perfect regioselectivity and in high enantioselectivity. The reaction shows a broad functional-group tolerance on both reaction partners highlighting its synthetic potential.
Rh-Catalysis: A regio- and enantioselective atom-economic catalytic addition of 1,3-diketones to allenes is reported furnishing tertiary and quaternary all-carbon stereocenters under mild reaction conditions. The reaction shows a broad functional-group tolerance and numerous variations on both reaction partners highlight its synthetic utility.
Acyclic quaternary centers from asymmetric conjugate addition of alkylzirconium reagents to linear trisubstituted enones
DOI: 10.1039/C6SC02811J, Edge Article
Synthetic methods for the selective formation of all carbon quaternary centres in non-cyclic systems are rare. Here we report highly enantioselective Cu-catalytic asymmetric conjugate addition of alkylzirconium species to twelve different acyclic trisubstituted enones.
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