Nickel/Bis(oxazoline)-Catalyzed Asymmetric Negishi Arylations of Racemic Secondary Benzylic Electrophiles to Generate Enantioenriched 1,1-Diarylalkanes

Nickel/Bis(oxazoline)-Catalyzed Asymmetric Negishi Arylations of Racemic Secondary Benzylic Electrophiles to Generate Enantioenriched 1,1-Diarylalkanes

A tertiary stereogenic center that bears two different aryl substituents is found in a variety of bioactive compounds, including medicines such as Zoloft and Detrol. We have developed an efficient method for the synthesis of enantioenriched 1,1-diarylalkanes from readily available racemic benzylic a...

Full description

Bibliographic Details
Main Authors:	Do, Hien-Quang, Chandrashekar, E. R. R., Fu, Gregory C
Other Authors:	Massachusetts Institute of Technology. Department of Chemistry
Format:	Article
Published:	American Chemical Society (ACS) 2018
Online Access:	http://hdl.handle.net/1721.1/113309

Similar Items

Nickel/Bis(oxazoline)-Catalyzed Asymmetric Kumada Reactions of Alkyl Electrophiles: Cross-Couplings of Racemic alpha-Bromoketones
by: Lou, Sha, et al.
Published: (2011)

Catalytic Enantioselective Cross-Couplings of Secondary Alkyl Electrophiles with Secondary Alkylmetal Nucleophiles: Negishi Reactions of Racemic Benzylic Bromides with Achiral Alkylzinc Reagents
by: Cordier, Christopher J., et al.
Published: (2013)

Palladium-Catalyzed Completely Linear-Selective Negishi Cross-Coupling of Allylzinc Halides with Aryl and Vinyl Electrophiles
by: Yang, Yang, et al.
Published: (2015)

Asymmetric Suzuki Cross-Couplings of Activated Secondary Alkyl Electrophiles: Arylations of Racemic α-Chloroamides
by: Lundin, Pamela M., et al.
Published: (2013)

Enantioconvergent Cross-Couplings of Racemic Alkylmetal Reagents with Unactivated Secondary Alkyl Electrophiles: Catalytic Asymmetric Negishi α-Alkylations of N-Boc-Pyrrolidine
by: Cordier, Christopher J., et al.
Published: (2018)

Alkene isomerization-hydroarylation tandem catalysis : indole C2-alkylation with aryl-substituted alkenes leading to 1,1-diarylalkanes
by: Yoshikai, Naohiko, et al.
Published: (2014)

Nickel-Catalyzed Asymmetric Negishi Cross-Couplings of Racemic Secondary Allylic Chlorides with Alkylzincs
by: Lou, Sha, et al.
Published: (2011)

Nickel-Catalyzed Enantioselective Negishi Cross-Couplings of Racemic Secondary alpha-Bromo Amides with Alkylzinc Reagents: (S)-N-Benzyl-7-cyano-2-ethyl-N-phenylheptanamide
by: Lou, Sha, et al.
Published: (2011)

Catalytic Asymmetric Synthesis of Tertiary Alkyl Fluorides: Negishi Cross-Couplings of Racemic α,α-Dihaloketones
by: Liang, Yufan, et al.
Published: (2015)

Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides
by: Han, Chong, et al.
Published: (2013)

Nickel-Catalyzed Enantioselective Cross-Couplings of Racemic Secondary Electrophiles That Bear an Oxygen Leaving Group
by: Oelke, Alexander J., et al.
Published: (2013)

Synthesis of Chiral Pyridine Bis(Oxazoline) Ligands for Nickel-Catalyzed Asymmetric Negishi Cross-Couplings of Secondary Allylic Chlorides with Alkylzincs: 2,6-bis[(4R)-4,5-dihydro-4- (2-phenylethyl)-2-oxazolyl]- Pyridine
by: Lou, Sha, et al.
Published: (2012)

Asymmetric Alkyl−Alkyl Cross-Couplings of Unactivated Secondary Alkyl Electrophiles: Stereoconvergent Suzuki Reactions of Racemic Acylated Halohydrins
by: Owston, Nathan A., et al.
Published: (2013)

Thiolate photocatalysis enables radical borylation of reductively inert aryl electrophiles
by: Li, Haoyu, et al.
Published: (2022)

Diastereoselective intramolecular hydride transfer triggered by electrophilic halogenation of aryl alkenes
by: Wang, Bin, et al.
Published: (2022)

Thiolate photocatalysis enables radical borylation of reductively inert aryl electrophiles
by: Li, Haoyu, et al.
Published: (2022)

1-[2,4,6-Trimethyl-3,5-bis(4-oxopiperidin-1-ylmethyl)benzyl]piperidin- 4-one
by: Rajesh, K., et al.
Published: (2010)

Ortho-C–H Benzylation of Aryl Imines with Benzyl Phosphates under Cobalt–Pyphos Catalysis
by: Xu, Wengang, et al.
Published: (2015)

Palladium-catalyzed enantioselective arylation of racemic ketones to form bridged bicycles via dynamic kinetic resolution
by: Huang, Xiaolei, et al.
Published: (2019)

Palladium-catalyzed, asymmetric Mizoroki–Heck reaction of benzylic electrophiles using phosphoramidites as chiral ligands
by: Yang, Zhigang, et al.
Published: (2013)

(E,E)-1,2-Bis[4-(prop-2-yn-1-yloxy)benzylidene]hydrazine
by: Al-Mehana, Wisam Naji Atiyah, et al.
Published: (2011)

Benzyl 2-{[2,8-bis(trifluoromethyl)-quinolin-4-yl](hydroxy)methyl}-piperidi ne-1-carboxylate
by: de Souza, M.V.N., et al.
Published: (2011)

Living Polymerization of 2-Ethylthio-2-oxazoline and Postpolymerization Diversification
by: Wu, You-Chi, et al.
Published: (2020)

1,3,2,5-Diazadiborinine featuring nucleophilic and electrophilic boron centres
by: Wu, Di, et al.
Published: (2015)

Benzyl N-[1-(furan-2-yl)ethylidene]hydrazinecarbodithioate.
by: Khoo, Teng Jin, et al.
Published: (2005)

Synthesis and characterization of cobalt(II), nickel(II), copper(II), zinc(II) and cadmium(II) complexes of benzyl N-[1-(thiophen-2-yl)ethylidene] hydrazine carbodithioate and benzyl N-[1-(thiophen-3-yl)ethylidene] hydrazine carbodithioate and the X-ray crystal structure of bis{benzyl N-[1-(thiophen-2-yl)ethylidene] hydrazine carbodithioate}nickel(II)
by: Chan, Eddy Mun Hoe, et al.
Published: (2008)

Synthesis of Solid 2-Pyridylzinc Reagents and Their Application in Negishi Reactions
by: Bernhardt, Sebastian, et al.
Published: (2015)

1,1 `-{[1,4-Phenylenebis(methylene)]bis(oxy)bis(3,1-phenylene)}diethanon e
by: Al-Mohammed, N.N., et al.
Published: (2011)

1,1 `-{[1,4-Phenylenebis(methylene)]bis(oxy)bis(4,1-phenylene)}diethanon e
by: Al-Mohammed, N.N., et al.
Published: (2011)

Syntheses of enantioenriched homoallylic hydroxylamines and ß-lactams using sugar template as the chiral auxiliary.
by: Wong, Shwo Mun.
Published: (2011)

A Modified System for the Synthesis of Enantioenriched N -Arylamines through Copper-Catalyzed Hydroamination
by: Ichikawa, Saki, et al.
Published: (2020)

Graphene Oxide as an Electrophile for Carbon Nucleophiles
by: Swager, Timothy Manning, et al.
Published: (2012)

Benzyl N '-(1-methyl-1H-indol-2-ylmethylene)hydrazinecarbodithioate
by: Khaledi, H., et al.
Published: (2008)

Benzyl N '-(1-methyl-1H-indol-3-ylmethylidene)hydrazinecarbodithioate
by: Khaledi, H., et al.
Published: (2008)

Benzyl N-{(1S)-2-hydroxy-1-[N'-(2-nitrobenzylidene)hydrazinylcarbonyl]ethyl\ carbamate
by: de Souza, M.V.N., et al.
Published: (2010)

Bis{benzyl 3- (1H-indol-3-yl)methylidene dithiocarbazato-kappa N-2(3),S}palladium(II) pyridine disolvate
by: Khaledi, H., et al.
Published: (2011)

Bis benzyl N '-(1H-indol-3-ylmethylene)hydrazinecarbodithioato-kappa(2)N ',S nickel(II) N,N-dimethylformamide disolvate
by: Khaledi, H., et al.
Published: (2008)

[mu-1,1 `-Bis(diphenylphosphino)ferrocene-kappa P-2:P `]bis[chloridogold(I)]-chloroform-hexane (2/2/1)
by: Meyer, N., et al.
Published: (2010)

1-Benzyl-2,5-dioxopyrrolidine-3,4-diyl diacetate
by: Caracelli, I., et al.
Published: (2010)

(Butane-1,3-diyne-1,4-diyl)bis(triisopropylsilane)
by: Shah, M.R., et al.
Published: (2010)