Literature DB >> 26799445

Synthesis of Strained γ-Lactams by Palladium(0)-Catalyzed C(sp(3) )-H Alkenylation and Application to Alkaloid Synthesis.

Philipp M Holstein1, David Dailler1,2, Julien Vantourout1, Janah Shaya1, Anthony Millet1, Olivier Baudoin3,4.   

Abstract

A variety of strained α-alkylidene-γ-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 plakoridine A and of the indolizidine alkaloid δ-coniceine.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−C coupling; C−H activation; natural products; nitrogen heterocycles; palladium

Mesh：

Substances：

Year:  2016        PMID： 26799445     DOI： 10.1002/anie.201511457

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  6 in total

1.  Formation of α-chiral centers by asymmetric β-C(sp3)-H arylation, alkenylation, and alkynylation.

Authors:  Qing-Feng Wu; Peng-Xiang Shen; Jian He; Xiao-Bing Wang; Forrest Zhang; Qian Shao; Ru-Yi Zhu; Claudio Mapelli; Jennifer X Qiao; Michael A Poss; Jin-Quan Yu
Journal:  Science       Date:  2017-02-03       Impact factor: 47.728

Review 2.  Complementary Strategies for Directed C(sp3 )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Authors:  John C K Chu; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-05       Impact factor: 15.336

3.  Palladium(0)-catalyzed asymmetric C(sp3)-H arylation using a chiral binol-derived phosphate and an achiral ligand.

Authors:  Lei Yang; Romain Melot; Markus Neuburger; Olivier Baudoin
Journal:  Chem Sci       Date:  2016-10-11       Impact factor: 9.825

4.  A Facile Direct Route to N-(Un)substituted Lactams by Cycloamination of Oxocarboxylic Acids without External Hydrogen.

Authors:  Hu Li; Hongguo Wu; Heng Zhang; Yaqiong Su; Song Yang; Emiel J M Hensen
Journal:  ChemSusChem       Date:  2019-07-17       Impact factor: 8.928

5.  Hypervalent iodine promoted the synthesis of cycloheptatrienes and cyclopropanes.

Authors:  Da-Fu Yuan; Zi-Chen Wang; Rui-Sen Geng; Guang-Yi Ren; James S Wright; Shao-Fei Ni; Ming Li; Li-Rong Wen; Lin-Bao Zhang
Journal:  Chem Sci       Date:  2021-12-08       Impact factor: 9.825

6.  C(sp3 )-H Arylation Promoted by a Heterogeneous Palladium-N-Heterocyclic Carbene Complex in Batch and Continuous Flow.

Authors:  Francesco Ferlin; Ioannis Anastasiou; Nihad Salameh; Takeru Miyakoshi; Olivier Baudoin; Luigi Vaccaro
Journal:  ChemSusChem       Date:  2022-02-18       Impact factor: 9.140
  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.