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

[1] Enantioselective synthesis of 2-methyl indolines by palladium catalysed asymmetric C(sp3)-H activation/cyclisation [J].