4.3 Article

Transition metal-catalyzed enantioselective C-P coupling reactions for the construction of P-stereogenic centers

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Article Chemistry, Organic

Ni-Catalyzed Enantioselective Benzylation of Secondary Phosphine Oxide

Wen-Qiang Cai et al.

Summary: The nickel-catalyzed benzylic substitution reaction of secondary phosphine oxide was described, providing dialkylated P-stereogenic tertiary phosphine oxides with high to excellent enantioselectivities. The reaction was performed under mild conditions using commercially available benzyl chlorides and bench-stable secondary phosphine oxides, and exhibited broad functional group tolerance. This work represents a practical example for the preparation of P-stereogenic phosphine compounds.

ORGANIC LETTERS (2022)

Article Chemistry, Multidisciplinary

Nickel/Bronsted acid dual-catalyzed regio- and enantioselective hydrophosphinylation of 1,3-dienes: access to chiral allylic phosphine oxides

Jiao Long et al.

Summary: The study introduces a novel asymmetric nickel/Bronsted acid dual-catalyzed reaction for the synthesis of chiral allylic phosphine oxides, featuring economic efficiency, broad substrate scope, and high selectivity. Preliminary mechanistic investigations suggest a highly regioselective process for 1,3-diene insertion into chiral Ni-H species and an irreversible step for chiral C-P bond formation.

CHEMICAL SCIENCE (2022)

Article Multidisciplinary Sciences

Enantioselective hydrogen-bond-donor catalysis to access diverse stereogenic-at-P(V) compounds

Katherine C. Forbes et al.

Summary: The stereoselective synthesis of molecules bearing stereogenic phosphorus (V) centers is a challenging task in organic chemistry. Existing methods rely on diastereocontrol using chiral auxiliaries, while catalytic, enantioselective methods offer an alternative approach.

SCIENCE (2022)

Article Chemistry, Multidisciplinary

Direct visible-light-induced synthesis of P-stereogenic phosphine oxides under air conditions

Ying Zhang et al.

Summary: Visible-light-induced reactions play an important role in organic synthesis, but efficient photochemical synthesis of enantiomerically pure molecules remains a challenge. This study describes a simple and efficient visible-light-induced reaction for the synthesis of P-chiral heteroaryl phosphine oxides.

CHEMICAL SCIENCE (2022)

Article Chemistry, Organic

Catalytic Asymmetric Synthesis of P-Stereogenic Phosphines: Beyond Precious Metals

David S. Glueck

Summary: Metal-catalyzed asymmetric synthesis of P-stereogenic phosphines can produce chiral ligands with valuable applications in asymmetric catalysis, without the need for precious metals. This method can be achieved using earth-abundant metals to develop more active catalysts.

SYNLETT (2021)

Article Chemistry, Multidisciplinary

Cobalt-Catalysed Asymmetric Addition and Alkylation of Secondary Phosphine Oxides for the Synthesis of P-Stereogenic Compounds

Zeng-Hua Wu et al.

Summary: Utilizing the pyridinyl moiety as the coordinating group in cobalt-catalysed asymmetric nucleophilic addition/alkylation of secondary phosphine oxides can lead to the efficient synthesis of tertiary phosphine oxides with high yields and high enantiomeric excess, along with broad functional-group tolerance. Mechanistic studies reveal that (R)-secondary phosphine oxides preferentially interact with the cobalt catalysts to produce P-stereogenic compounds.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Carbene-Catalyzed Enantioselective Hydrophosphination of α-Bromoenals to Prepare Phosphine-Containing Chiral Molecules

Rakesh Maiti et al.

Summary: This study presents a novel carbene-catalyzed reaction for the efficient synthesis of chiral phosphines. These phosphines can serve as chiral ligands or catalysts with broad applications in asymmetric catalysis.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Palladium/Xiao-Phos-Catalyzed Kinetic Resolution of sec-Phosphine Oxides by P-Benzylation

Qiang Dai et al.

Summary: This study successfully achieved the kinetic resolution of rac-secondary phosphine oxides via enantioselective P-benzylation catalysis, delivering both tert- and sec-phosphine oxides in good yield and excellent enantiopurity. The synthetic utilities were further demonstrated by the facile preparation of valuable P-chiral compounds, precursors of bidentate ligands, and transition metal complexes.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Organic

Ni-Catalyzed Enantioselective Allylic Alkylation of H-Phosphinates

Qing Zhang et al.

Summary: The asymmetric synthesis of allylic P-stereogenic phosphinates from H-phosphinates has been successfully developed, achieving high enantioselectivities of up to 92% ee and generally high yields. Furthermore, this method is applicable for scale-up synthesis and facile transformation of chiral products from phosphinates to phosphine oxides under mild reaction conditions, demonstrating its versatility and practicality.

ORGANIC LETTERS (2021)

Article Chemistry, Physical

Iridium-Catalyzed Enantioselective C-H Borylation of Diarylphosphinates

Shu-Yong Song et al.

Summary: This study presents a novel method for the synthesis of P-stereogenic phosphorus compounds through phosphinate-directed iridium-catalyzed reactions, with high yields and good enantioselectivities. The borylated products synthesized can be used for the preparation of precursors for chiral phosphine ligands, showing potential industrial applications.

ACS CATALYSIS (2021)

Article Chemistry, Multidisciplinary

Asymmetric Synthesis of P-Stereogenic Secondary Phosphine-Boranes by an Unsymmetric Bisphosphine Pincer-Nickel Complex

Chuanyong Wang et al.

Summary: The first highly enantioselective catalytic synthesis of P-stereogenic secondary phosphine-boranes was achieved using a newly developed unsymmetric bisphosphine pincer-nickel complex. Various P-stereogenic secondary phosphine-boranes were obtained in good yields with high enantioselectivity and diastereoselectivity. Subsequent alkylation upon P-C bond formation provided a practical way to access P-chiral compounds with diverse functional groups.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Multidisciplinary

Ni-Catalyzed Asymmetric Hydrophosphination of Unactivated Alkynes

Xu-Teng Liu et al.

Summary: The regio- and enantioselective hydrophosphination using a nickel complex catalyzed reaction has successfully synthesized P-stereogenic tertiary phosphines with wide applications. The products obtained through this method can be easily converted into various precursors of bidentate ligands and transition metal complexes, demonstrating unprecedented substrate scope and functional group compatibility. This presents new opportunities for asymmetric catalysis, materials, and pharmaceutical chemistry.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Multidisciplinary

Copper(I)-Catalyzed Asymmetric Alkylation of Unsymmetrical Secondary Phosphines

Shuai Zhang et al.

Summary: A copper(I)-catalyzed asymmetric alkylation reaction has been developed, providing an array of P-stereogenic phosphines in high yield and enantioselectivity. This methodology is also applicable to catalytic asymmetric double and triple alkylation reactions, yielding products with moderate diastereo- and excellent enantioselectivities. The high enantioselectivity is attributed to the performance of the unique Cu(I)-(R,RP)-TANIAPHOS complex in asymmetric induction.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Physical

Ligand-Enabled Copper(I)-Catalyzed Asymmetric Radical C(sp(3))-C Cross-Coupling Reactions

Huan Zhou et al.

Summary: Transition-metal-catalyzed asymmetric C-(sp(3))-C cross-coupling is an efficient method for the rapid synthesis of enantioenriched molecules. Chiral copper catalysts have been designed to promote a variety of asymmetric radical C(sp(3))-C cross-coupling reactions with high efficiency and enantioselectivity. The key to success lies in the design of chiral ligands to initiate the reaction and achieve enantiocontrol over the highly reactive prochiral alkyl radical species.

ACS CATALYSIS (2021)

Article Chemistry, Multidisciplinary

Access to P-stereogenic compounds via desymmetrizing enantioselective bromination

Qiu-Hong Huang et al.

Summary: An efficient desymmetrizing asymmetric ortho-selective mono-bromination of bisphenol phosphine oxides under chiral squaramide catalysis was reported, leading to a variety of chiral products with high yields and enantioselectivities. The reaction could be scaled up for practical use, demonstrating the synthetic utility of the P-stereogenic compounds in asymmetric reactions.

CHEMICAL SCIENCE (2021)

Article Chemistry, Multidisciplinary

Rapid Synthesis of Chiral 1,2-Bisphosphine Derivatives through Copper(I)-Catalyzed Asymmetric Conjugate Hydrophosphination

Yue Wen-Jun et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Multidisciplinary Sciences

Enantioselective remote C-H activation directed by a chiral cation

Georgi R. Genov et al.

SCIENCE (2020)

Article Chemistry, Multidisciplinary

Construction of P-Chiral Alkenylphosphine Oxides through Highly Chemo-, Regio-, and Enantioselective Hydrophosphinylation of Alkynes

Qiang Dai et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Catalytic Asymmetric Synthesis of the anti-COVID-19 Drug Remdesivir

Mo Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Review Multidisciplinary Sciences

Using nature's blueprint to expand catalysis with Earth-abundant metals

R. Morris Bullock et al.

SCIENCE (2020)

Article Chemistry, Multidisciplinary

Copper(I)-Catalyzed Asymmetric 1,4-Conjugate Hydrophosphination of α,β-Unsaturated Amides

Yan-Bo Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Synthesis of P-chiral phosphine compounds by palladium-catalyzed C-P coupling reactions

Cuiying Wang et al.

CHEMICAL COMMUNICATIONS (2020)

Review Chemistry, Multidisciplinary

Recent Advances in Catalytic Asymmetric Synthesis of P-Chiral Phosphine Oxides

Ren-Yi Zhu et al.

ACTA CHIMICA SINICA (2020)

Review Biochemistry & Molecular Biology

Natural Products Containing 'Rare' Organophosphorus Functional Groups

Janusz J. Petkowski et al.

MOLECULES (2019)

Review Chemistry, Physical

Generation of Heteroatom Stereocenters by Enantioselective C-H Functionalization

Johannes Diesel et al.

ACS CATALYSIS (2019)

Article Chemistry, Multidisciplinary

Ni-Catalyzed Asymmetric Allylation of Secondary Phosphine Oxides

Xu-Teng Liu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Access to P-chiral phosphine oxides by enantioselective allylic alkylation of bisphenols

Guo-Hui Yang et al.

CHEMICAL SCIENCE (2019)

Review Chemistry, Multidisciplinary

Applications and stereoselective syntheses of P-chirogenic phosphorus compounds

Mathieu Dutartre et al.

CHEMICAL SOCIETY REVIEWS (2016)

Article Chemistry, Multidisciplinary

Enantioselective Cu-Catalyzed Arylation of Secondary Phosphine Oxides with Diaryliodonium Salts toward the Synthesis of P-Chiral Phosphines

Rodolphe Beaud et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

Access to P-Stereogenic Phosphinates via N-Heterocyclic Carbene-Catalyzed Desymmetrization of Bisphenols

Zhijian Huang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Review Multidisciplinary Sciences

Recent advances in homogeneous nickel catalysis

Sarah Z. Tasker et al.

NATURE (2014)

Review Chemistry, Inorganic & Nuclear

Secondary phosphine oxides: Versatile ligands in transition metal-catalyzed cross-coupling reactions

Tanveer Mahamadali Shaikh et al.

COORDINATION CHEMISTRY REVIEWS (2012)

Article Chemistry, Organic

Room Temperature, Palladium-Mediated P-Arylation of Secondary Phosphine Oxides

Aaron J. Bloomfield et al.

ORGANIC LETTERS (2012)

Article Chemistry, Inorganic & Nuclear

Recent developments in the asymmetric synthesis of P-chiral phosphorus compounds

Oleg I. Kolodiazhnyi

TETRAHEDRON-ASYMMETRY (2012)

Article Chemistry, Multidisciplinary

Nickel-Catalyzed C-P Cross-Coupling by C-CN Bond Cleavage

Meng Sun et al.

CHEMISTRY-A EUROPEAN JOURNAL (2011)

Article Chemistry, Multidisciplinary

Development of Ruthenium Catalysts for the Enantioselective Synthesis of P-Stereogenic Phosphines via Nucleophilic Phosphido Intermediates

Vincent S. Chan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

Article Chemistry, Multidisciplinary

Catalytic asymmetric synthesis of chiral phosphanes

David S. Glueck

CHEMISTRY-A EUROPEAN JOURNAL (2008)

Article Chemistry, Multidisciplinary

Pd-catalyzed dynamic kinetic enantioselective arylation of silylphosphines

Vincent S. Chan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

Article Chemistry, Organic

Metal-catalyzed asymmetric synthesis of P-stereogenic Phosphines

David S. Glueck

SYNLETT (2007)

Article Chemistry, Multidisciplinary

Palladium-catalyzed asymmetric phosphination. Scope, mechanism, and origin of enantioselectivity

Natalia F. Blank et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

Article Chemistry, Multidisciplinary

Asymmetric catalytic synthesis of P-stereogenic phosphines via a nucleophilic ruthenium phosphido complex

VS Chan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Article Chemistry, Multidisciplinary

Platinum-catalyzed asymmetric alkylation of secondary phosphines: Enantioselective synthesis of P-stereogenic phosphines

C Scriban et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Article Chemistry, Multidisciplinary

Preparation of chiral triarylphosphines by Pd-catalysed asymmetric P-C cross-coupling

C Korff et al.

CHEMICAL COMMUNICATIONS (2004)

Article Chemistry, Multidisciplinary

Palladium-catalyzed asymmetric phosphination: Enantioselective synthesis of a P-chirogenic phosphine

JR Moncarz et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2002)