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

[51] TBHP-promoted direct oxidation reaction of benzylic Csp3-H bonds to ketones [J].

Tan, Jiajing ;

Zheng, Tianyu ;

Yu, Yuqi ;

Xu, Kun .

RSC ADVANCES, 2017, 7 (25) :15176-15180

[52]

Tasker SZ, 2014, NATURE, V509, P299, DOI 10.1038/nature13274

[53] An efficient and stereoselective cycloaddition of C-aryl and C-amido nitrones to dimethyl 2-benzylidenecyclopropane-1,1-dicarboxylate [J].

Tran, Tung Q. ;

Diev, Vyacheslav V. ;

Molchanov, Alexander P. .

TETRAHEDRON, 2011, 67 (13) :2391-2395

[54] UNSATURATED CYCLOPROPANES .3. SYNTHESIS AND PROPERTIES OF ALKYLIDENECYCLOPROPANES AND SPIROPENTANES [J].

ULLMAN, EF ;

FANSHAWE, WJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (10) :2379-&

[55] HEATS OF FORMATION OF C4H6 HYDROCARBONS [J].

WIBERG, KB ;

FENOGLIO, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (13) :3395-&

[56]

Wu Zhimeng, 2009, Antivir Chem Chemother, V20, P37, DOI 10.3851/IMP782

[57] The Construction of Molecular Complexity from Functionalized Alkylidenecyclopropanes (FACPs) [J].

Yu, Liu-Zhu ;

Shi, Min .

CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (32) :7591-7606

[58] Recent advances in the chemical transformations of functionalized alkylidenecyclopropanes (FACPs) [J].

Yu, Liu-Zhu ;

Chen, Kai ;

Zhu, Zi-Zhong ;

Shi, Min .

CHEMICAL COMMUNICATIONS, 2017, 53 (44) :5935-5945

[59] Regio- and Enantioselective C-H Cyclization of Pyridines with Alkenes Enabled by a Nickel/N-Heterocyclic Carbene Catalysis [J].

Zhang, Wu-Bin ;

Yang, Xin-Tuo ;

Ma, Jun-Bao ;

Su, Zhi-Ming ;

Shi, Shi-Liang .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (14) :5628-5634

[60] Synthesis and antiviral activity of (Z)- and (E)-2,2-[bis(hydroxymethyl)cyclopropylidene]methylpurines and -pyrimidines:: Second-generation methylenecyclopropane analogues of nucleosides [J].

Zhou, SM ;

Breitenbach, JM ;

Borysko, KZ ;

Drach, JC ;

Kern, ER ;

Gullen, E ;

Cheng, YC ;

Zemlicka, J .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (03) :566-575

← 1 2 3 4 5 6 7 →