A Chiral Naphthyridine Diimine Ligand Enables Nickel-Catalyzed Asymmetric Alkylidenecyclopropanations

被引：20

作者：

Braconi, Elena ^{[1
]}

Cramer, Nicolai ^{[1
]}

机构：

[1] EPFL SB ISIC LCSA, Inst Chem Sci & Engn ISIC, BCH 4305, CH-1015 Lausanne, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 38期

基金：

瑞士国家科学基金会;

关键词：

alkylidene transfer; asymmetric catalysis; cyclopropanes; naphthyridine diimine (NDI) ligands; nickel; DIELS-ALDER REACTIONS; HYDROGENATION; COMPLEXES; ALKYNES; METHYLENECYCLOPROPANES; CYCLOPROPANATION; TRANSFORMATIONS; DERIVATIVES; ACCESS; BONDS;

D O I：

10.1002/anie.202006082

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel class of chiral naphthyridine diimine ligands (NDI*) readily accessible fromC(2)-symmetric 2,6-di-(1-arylethyl)anilines is described. The utility of these ligands, particularly one with fluorinated aryl side arms, is demonstrated by a reductive Ni-catalyzed enantioselective alkylidene transfer reaction from 1,1-dichloroalkenes to olefins. This transformation provides direct access to a broad range of synthetically valuable alkylidenecyclopropanes in high yields and enantioselectivities.

引用

页码：16425 / 16429

页数：5

共 64 条

[1]

Ahlin, 2014, ANGEW CHEM, V126, P13445

[2] Chiral N-Heterocyclic Carbene Ligand Enabled Nickel(0)-Catalyzed Enantioselective Three-Component Couplings as Direct Access to Silylated Indanols [J].

Ahlin, Joachim S. E. ;

Cramer, Nicolai .

ORGANIC LETTERS, 2016, 18 (13) :3242-3245

[3] Nickel(0)-Catalyzed Enantioselective Annulations of Alkynes and Arylenoates Enabled by a Chiral NHC Ligand: Efficient Access to Cyclopentenones [J].

Ahlin, Joachim S. E. ;

Donets, Pavel A. ;

Cramer, Nicolai .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (48) :13229-13233

[4] Application of a C2-Symmetric Copper Carbenoid in the Enantioselective Hydrosilylation of Dialkyl and Aryl-Alkyl Ketones [J].

Albright, Abigail ;

Gawley, Robert E. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (49) :19680-19683

[5] Design and Synthesis of C2-Symmetric N-Heterocyclic Carbene Precursors and Metal Carbenoids [J].

Albright, Abigail ;

Eddings, Daniel ;

Black, Regina ;

Welch, Christopher J. ;

Gerasimchuk, Nikolay N. ;

Gawley, Robert E. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (18) :7341-7351

[6]

[Anonymous], ANGEW CHEM

[7]

[Anonymous], 2020, NICKEL CATALYSIS ORG

[8] Synthesis of Methylene- and Alkylidenecyclopropane Derivatives [J].

Audran, Gerard ;

Pellissier, Helene .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (04) :575-608

[9] Strain energy of small ring hydrocarbons. Influence of C-H bond dissociation energies [J].

Bach, RD ;

Dmitrenko, O .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4444-4452

[10] [2+1] cycloadditions of terminal alkynes to norbornene derivatives catalyzed by palladium complexes with phosphinous acid ligands [J].

Bigeault, J ;

Giordano, L ;

Buono, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (30) :4753-4757

← 1 2 3 4 5 6 7 →