Stereospecific nickel-catalyzed cross-coupling reactions of alkyl Grignard reagents and identification of selective anti-breast-cancer agents.

Alkyl Grignard reagents that contain β-hydrogen atoms were used in a stereospecific nickel-catalyzed cross-coupling reaction to form C(sp(3))-C(sp(3)) bonds. Aryl Grignard reagents were also utilized to synthesize 1,1-diarylalkanes. Several compounds synthesized by this method exhibited selective inhibition of proliferation of MCF-7 breast cancer cells.

[1]  R. Jana,et al.  Pd(0)-catalyzed 1,1-diarylation of ethylene and allylic carbonates. , 2013, Organic letters.

[2]  A. Doyle,et al.  Directed nickel-catalyzed negishi cross coupling of alkyl aziridines. , 2013, Journal of the American Chemical Society.

[3]  E. R. Jarvo,et al.  Asymmetric transition metal-catalyzed cross-coupling reactions for the construction of tertiary stereocenters. , 2013, Tetrahedron.

[4]  C. Cordier,et al.  Enantioconvergent cross-couplings of racemic alkylmetal reagents with unactivated secondary alkyl electrophiles: catalytic asymmetric Negishi α-alkylations of N-Boc-pyrrolidine. , 2013, Journal of the American Chemical Society.

[5]  E. R. Jarvo,et al.  Functional-group-tolerant, nickel-catalyzed cross-coupling reaction for enantioselective construction of tertiary methyl-bearing stereocenters. , 2013, Journal of the American Chemical Society.

[6]  S. Rychnovsky,et al.  Determination of absolute configuration of secondary alcohols using thin-layer chromatography. , 2013, The Journal of organic chemistry.

[7]  C. Moore,et al.  Retention or inversion in stereospecific nickel-catalyzed cross-coupling of benzylic carbamates with arylboronic esters: control of absolute stereochemistry with an achiral catalyst. , 2013, Journal of the American Chemical Society.

[8]  S. Dasgupta,et al.  Nickel-catalyzed cross-couplings of benzylic pivalates with arylboroxines: stereospecific formation of diarylalkanes and triarylmethanes. , 2013, Journal of the American Chemical Society.

[9]  G. Yap,et al.  Nickel-catalyzed cross couplings of benzylic ammonium salts and boronic acids: stereospecific formation of diarylethanes via C-N bond activation. , 2013, Journal of the American Chemical Society.

[10]  B. Taylor,et al.  Synthesis of enantioenriched triarylmethanes by stereospecific cross-coupling reactions. , 2012, Angewandte Chemie.

[11]  B. Welm,et al.  Synthesis and preliminary biological study of bisindolylmethanes accessed by an acid-catalyzed hydroarylation of vinyl indoles , 2012 .

[12]  G. C. Fu,et al.  Catalytic asymmetric synthesis of secondary nitriles via stereoconvergent Negishi arylations and alkenylations of racemic α-bromonitriles. , 2012, Journal of the American Chemical Society.

[13]  E. R. Jarvo,et al.  Traceless directing group for stereospecific nickel-catalyzed alkyl-alkyl cross-coupling reactions. , 2012, Organic letters.

[14]  M. Burke,et al.  Pinene-Derived Iminodiacetic Acid (PIDA): A Powerful Ligand for Stereoselective Synthesis and Iterative Cross-Coupling of C(sp3) Boronate Building Blocks , 2011, Journal of the American Chemical Society.

[15]  R. Jana,et al.  Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners. , 2011, Chemical reviews.

[16]  Jack Hu,et al.  Highly enantioselective hydrogenation of styrenes directed by 2'-hydroxyl groups. , 2011, Organic letters.

[17]  J. Wdzieczak‐Bakala,et al.  Discovery of Isoerianin Analogues as Promising Anticancer Agents , 2011, ChemMedChem.

[18]  Joshua D. Waetzig,et al.  Stereospecific nickel-catalyzed cross-coupling reactions of alkyl ethers: enantioselective synthesis of diarylethanes. , 2011, Journal of the American Chemical Society.

[19]  B. Welm,et al.  Synthesis and preliminary biological studies of 3-substituted indoles accessed by a palladium-catalyzed enantioselective alkene difunctionalization reaction. , 2010, Journal of the American Chemical Society.

[20]  Ulrike E. Hille,et al.  Isopropylidene substitution increases activity and selectivity of biphenylmethylene 4-pyridine type CYP17 inhibitors. , 2010, Journal of medicinal chemistry.

[21]  J. Adrio,et al.  Palladium-catalyzed cross-coupling reaction of secondary benzylic bromides with grignard reagents. , 2009, Organic letters.

[22]  Ben W. Glasspoole,et al.  Cross coupling reactions of chiral secondary organoboronic esters with retention of configuration. , 2009, Journal of the American Chemical Society.

[23]  F. Glorius.  Asymmetrische Kreuzkupplung von nicht‐aktivierten sekundären Alkylhalogeniden , 2008 .

[24]  F. Glorius.  Asymmetric cross-coupling of non-activated secondary alkyl halides. , 2008, Angewandte Chemie.

[25]  D. Phillips,et al.  Density functional theory studies of negishi alkyl-alkyl cross-coupling reactions catalyzed by a methylterpyridyl-Ni(I) complex. , 2008, The Journal of organic chemistry.

[26]  L. Wessjohann,et al.  Acceleration of arylzinc formation and its enantioselective addition to aldehydes by microwave irradiation and aziridine-2-methanol catalysts. , 2008, The Journal of organic chemistry.

[27]  Erick M. Carreira,et al.  Enantioselektive Synthese von 1,1‐Diarylethanen: Aldehyde als entfernbare Steuerungsgruppen in der asymmetrischen Synthese , 2007 .

[28]  S. P. Andrews,et al.  Enantioselective preparation of 1,1-diarylethanes: aldehydes as removable steering groups for asymmetric synthesis. , 2007, Angewandte Chemie.

[29]  S. Shimada,et al.  Ni-catalyzed addition reaction of allylic selenides to alkynes , 2007 .

[30]  P. Pulay,et al.  Ligand redox effects in the synthesis, electronic structure, and reactivity of an alkyl-alkyl cross-coupling catalyst. , 2006, Journal of the American Chemical Society.

[31]  Anthony Howell,et al.  Pure oestrogen antagonists for the treatment of advanced breast cancer. , 2006, Endocrine-related cancer.

[32]  M. Makishima,et al.  Diphenylmethane skeleton as a multi-template for nuclear receptor ligands: preparation of FXR and PPAR ligands. , 2006, Bioorganic & medicinal chemistry letters.

[33]  C. Bolm,et al.  Catalyzed asymmetric aryl transfer reactions to aldehydes with boronic acids as aryl source. , 2002, Journal of the American Chemical Society.

[34]  E. Corey,et al.  Reduction of Carbonyl Compounds with Chiral Oxazaborolidine Catalysts: A New Paradigm for Enantioselective Catalysis and a Powerful New Synthetic Method. , 1998, Angewandte Chemie.

[35]  E. J. Corey,et al.  Reduktion von Carbonylverbindungen mit chiralen Oxazaborolidin‐Katalysatoren: eine neue enantioselektive Katalyse und leistungsfähige Synthesemethode , 1998 .

[36]  A. Chan,et al.  Enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by Ti(BINOL) complex , 1997 .

[37]  J. Fiaud,et al.  Palladium-catalyzed substitution of esters of naphthylmethanols, 1-naphthylethanols, and analogues by sodium dimethyl malonate. Stereoselective synthesis from enantiomerically pure substrates , 1995 .

[38]  J. Bäckvall,et al.  Correction. Isomerization of (π-Allyl)Palladium Complexes via Nucleophilic Displacement by Palladium(0). A Common Mechanism in Palladium(0)-Catalyzed Allylic Substitution , 1992 .

[39]  A. Wakeling,et al.  A potent specific pure antiestrogen with clinical potential. , 1991, Cancer research.

[40]  Y. Tanigawa,et al.  Palladium(0)-catalyzed azidation of allyl esters. Selective synthesis of allyl azides, primary allylamines, and related compounds , 1989 .

[41]  J. Kochi.  The role of electron transfer and charge transfer in organometallic chemistry , 1980 .

[42]  J. Stille,et al.  The oxidative addition of benzyl halides to tetrakis(triphenylphosphine)nickel(O) , 1977 .

[43]  A. Johnson.  Stereospecific Nickel-Catalyzed Cross-Coupling Reactions , 2015 .

[44]  R. Noyori,et al.  Enantioselective Addition of Organometallic Reagents to Carbonyl Compounds: Chirality Transfer, Multiplication, and Amplification† , 1991 .

[45]  R. Noyori,et al.  Enantioselektive Addition von Organometallreagentien an Carbonylverbindungen: Übertragung, Vervielfältigung und Verstärkung der Chiralität , 1991 .

[46]  K. Fisher,et al.  Metal vapour synthesis of zero-valent nickel phosphine complexes and their characterization by 31P NMR spectroscopy , 1989 .