1402852-05-4Relevant academic research and scientific papers
Cu-Catalyzed Diastereo- and Enantioselective Reactions of γ,γ-Disubstituted Allyldiboron Compounds with Ketones
Meek, Simon J.,Zanghi, Joseph M.
, p. 8451 - 8455 (2020)
A catalytic diastereo- and enantioselective method for the preparation of complex tertiary homoallylic alcohols containing a vicinal quaternary carbon stereogenic center and a versatile alkenylboronic ester is disclosed. Transformations are promoted by 5 mol % of a readily available copper catalyst bearing a bulky monodentate phosphoramidite ligand, which is essential for attaining both high dr and er. Reactions proceed with a wide variety of ketones and allylic 1,1-diboronate reagents, which enables the efficient preparation of diverse array of molecular scaffolds.
Enantioselective Synthesis of Functionalized Arenes by Nickel-Catalyzed Site-Selective Hydroarylation of 1,3-Dienes with Aryl Boronates
Marcum, Justin S.,Meek, Simon J.,Taylor, Tiffany R.
, p. 14070 - 14075 (2020/06/10)
A catalytic method for the site-selective and enantioselective synthesis of functionalized arenes by the intermolecular hydroarylation of terminal and internal 1,3-dienes with aryl pinacolato boronates is reported. The reactions are promoted by 5.0 mol %
Diastereo- A nd Enantioselective Synthesis of Homoallylic Amines Bearing Quaternary Carbon Centers
Green, Jacob C.,Zanghi, Joseph M.,Meek, Simon J.
supporting information, p. 1704 - 1709 (2020/02/20)
A Cu-catalyzed method for the efficient enantio- A nd diastereoselective synthesis of chiral homoallylic amines bearing a quaternary carbon and an alkenylboron is disclosed. Transformations are promoted by a readily prepared (phosphoramidite)-Cu complex and involve bench-stable ?,?-disubstituted allyldiborons and benzyl imines; products are obtained in up to 82% yield, >20:1 dr, and >99:1 er. Reactions proceed via stereodefined boron-stabilized allylic Cu species formed by an enantioselective transmetalation. Utility of the 1-amino-3-alkenylboronate products is highlighted by a variety of synthetic transformations.
Transition metal complexes of N-heterocyclic carbenes, method of preparation and use in transition metal catalyzed organic transformations
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Page/Page column 11; 16, (2010/11/26)
The present invention relates to catalysts of transition metal complexes of N-heterocyclic carbenes, their methods of preparation and their use in chemical synthesis. The synthesis, ease-of-use, and activity of the compounds of the present invention are substantial improvements over in situ catalyst generation. Further, the transition metal complexes of N-heterocyclic carbenes of the present invention may be used as precatalysts in metal-catalyzed cross-coupling reactions.
Easily prepared air- and moisture-stable Pd-NHC (NHC = N-heterocyclic carbene) complexes: A reliable, user-friendly, highly active palladium precatalyst for the Suzuki-Miyaura reaction
O'Brien, Christopher J.,Kantchev, Eric Assen B.,Valente, Cory,Hadei, Niloufar,Chass, Gregory A.,Lough, Alan,Hopkinson, Alan C.,Organ, Michael G.
, p. 4743 - 4748 (2008/02/08)
The synthesis of NHC-PdCl2-3-chloropyridine (NHC = N-heterocyclic carbene) complexes from readily available starting materials in air is described. The 2,6-diisopropylphenyl derivative was found to be highly catalytically active in alkyl-alkyl Suzuki and Negishi cross-coupling reactions. The synthesis, ease-of-use, and activity of this complex are substantial improvements over in situ catalyst generation and all current Pd-NHC complexes. The utilization of complex 4 led to the development of a reliable, easily employed Suzuki-Miyama protocol. Employing various reaction conditions allowed a large array of hindered biaryl and drug-like heteroaromatic compounds to be synthesized without difficulty.
The development of the asymmetric Morita-Baylis-Hillman reaction catalyzed by chiral Bronsted acids
McDougal, Nolan T.,Trevellini, Whitney L.,Rodgen, Stacy A.,Kliman, Laura T.,Schaus, Scott E.
, p. 1231 - 1240 (2007/10/03)
This report describes the development of a chiral Bronsted acid-catalyzed asymmetric Morita-Baylis-Hillman (MBH) reaction of cyclohexenone with aldehydes. During the course of our studies on chiral Lewis acid-promoted MBH reactions, we discovered that chi
Asymmetric Morita-Baylis-Hillman reactions catalyzed by chiral Bronsted acids
McDougal, Nolan T.,Schaus, Scott E.
, p. 12094 - 12095 (2007/10/03)
Chiral BINOL-derived Bronsted acids catalyze the enantioselective asymmetric Morita-Baylis-Hillman (MBH) reaction of cyclohexenone with aldehydes. The asymmetric MBH reaction requires 2-20 mol % of the chiral Bronsted acid 2e or 2f and triethylphosphine a
