Synthesis of Strained γ-Lactams by Palladium(0)-Catalyzed C(sp3)-H Alkenylation and Application to Alkaloid Synthesis

被引：52

作者：

Holstein, Philipp M. ^{[1
]}

Dallier, David ^{[1
,2
]}

Vantourout, Julien ^{[1
]}

Shaya, Janah ^{[1
]}

Millet, Anthony ^{[1
]}

Baudoin, Olivier ^{[1
,2
]}

机构：

[1] Univ Lyon 1, CNRS UMR 5246, Inst Chim & Biochim Mol & Supramol, CPE Lyon, 43 Blvd 11 Novembre 1918, F-69622 Villeurbanne, France

[2] Univ Basel, Dept Chem, St Johanns Ring 19, CH-4056 Basel, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 08期

关键词：

C-C coupling; C-H activation; natural products; nitrogen heterocycles; palladium; C-H ACTIVATION; INTRAMOLECULAR ALKANE ARYLATION; DELTA-CONICEINE; ASYMMETRIC-SYNTHESIS; FACILE SYNTHESIS; FUNCTIONALIZATION; INDOLINES; DERIVATIVES; ACCESS; BONDS;

D O I：

10.1002/anie.201511457

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A variety of strained alpha-alkylidene-gamma-lactams were synthesized by palladium(0)-catalyzed intramolecular C(sp(3))-H alkenylation from easily accessible acyclic and monocyclic bromoalkene precursors. These lactams are valuable intermediates for accessing various classes of mono- and bicylic alkaloids containing a pyrrolidine ring, as illustrated with the synthesis of an advanced model of the marine natural product plakoridineA and of the indolizidine alkaloid delta-coniceine.

引用

页码：2805 / 2809

页数：5

共 66 条

[31] Palladium-catalyzed ring-opening of cyclopropyl benzamides: synthesis of benzo[c]azepine-1-ones via C(sp3)-H functionalization [J].

Ladd, Carolyn L. ;

Roman, Daniela Sustac ;

Charette, Andre B. .

TETRAHEDRON, 2013, 69 (22) :4479-4487

[32] Silver-Promoted, Palladium-Catalyzed Direct Arylation of Cyclopropanes: Facile Access to Spiro 3,3′-Cyclopropyl Oxindoles [J].

Ladd, Carolyn L. ;

Roman, Daniela Sustac ;

Charette, Andre B. .

ORGANIC LETTERS, 2013, 15 (06) :1350-1353

[33] High-yielding palladium-catalyzed intramolecular alkane arylation: Reaction development and mechanistic studies [J].

Lafrance, Marc ;

Gorelsky, Serge I. ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (47) :14570-+

[34] Scope and mechanism of asymmetric C(sp3)-H/C(Ar)-X coupling reactions: computational and experimental study [J].

Larionov, Evgeny ;

Nakanishi, Masafumi ;

Katayev, Dmitry ;

Besnard, Celine ;

Kuendig, E. Peter .

CHEMICAL SCIENCE, 2013, 4 (05) :1995-2005

[35] Challenge and progress: palladium-catalyzed sp3 C-H activation [J].

Li, Hu ;

Lia, Bi-Jie ;

Shi, Zhang-Jie .

CATALYSIS SCIENCE & TECHNOLOGY, 2011, 1 (02) :191-206

[36] Diastereo- and Enantioselective Intramolecular C(sp3)?H Arylation for the Synthesis of Fused Cyclopentanes [J].

Martin, Nicolas ;

Pierre, Cathleen ;

Davi, Michael ;

Jazzar, Rodolphe ;

Baudoin, Olivier .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (15) :4480-4484

[37] Indolizidine and quinolizidine alkaloids [J].

Michael, Joseph P. .

NATURAL PRODUCT REPORTS, 2008, 25 (01) :139-165

[38] Fused Indolines by Palladium-Catalyzed Asymmetric C-C Coupling Involving an Unactivated Methylene Group [J].

Nakanishi, Masafumi ;

Katayev, Dmitry ;

Besnard, Celine ;

Kuendig, E. Peter .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (32) :7438-7441

[39] Pyrrole, pyrrolidine, pyridine, piperidine and tropane alkaloids [J].

O'Hagan, D .

NATURAL PRODUCT REPORTS, 2000, 17 (05) :435-446

[40]

Pedroni J., 2014, ANGEW CHEM, V126, P9210

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