Literature DB >> 25960013

Silver(I)- or copper(II)-mediated dearomatization of aromatic ynones: direct access to spirocyclic scaffolds.

Michael J James1, James D Cuthbertson1, Peter O'Brien1, Richard J K Taylor2, William P Unsworth3.   

Abstract

A high-yielding silver(I)- or copper(II)-catalyzed dearomatizing spirocyclization strategy allows the conversion of simple aromatic compounds that contain ynone substituents, including indole, anisole, pyrrole, and benzofuran derivatives, into functionalized spirocyclic scaffolds. A high-yielding asymmetric variant furnishes spirocyclic indolenines in up to 89:11 e.r.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric catalysis; dearomatization; indolenines; silver; spirocycles

Year:  2015        PMID： 25960013     DOI： 10.1002/anie.201501812

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


  6 in total

1.  A Thiol-Mediated Three-Step Ring Expansion Cascade for the Conversion of Indoles into Functionalized Quinolines.

Authors:  Nantachai Inprung; Michael J James; Richard J K Taylor; William P Unsworth
Journal:  Org Lett       Date:  2021-03-01       Impact factor: 6.005

2.  Total synthesis of (+)-spiroindimicin A and congeners unveils their antiparasitic activity.

Authors:  Zhen Zhang; Sneha Ray; Leah Imlay; Lauren T Callaghan; Hanspeter Niederstrasser; Prema Latha Mallipeddi; Bruce A Posner; Dawn M Wetzel; Margaret A Phillips; Myles W Smith
Journal:  Chem Sci       Date:  2021-06-30       Impact factor: 9.825

3.  Selectivity, Speciation, and Substrate Control in the Gold-Catalyzed Coupling of Indoles and Alkynes.

Authors:  Ryan G Epton; William P Unsworth; Jason M Lynam
Journal:  Organometallics       Date:  2022-02-10       Impact factor: 3.876

4.  Catalyst-Driven Scaffold Diversity: Selective Synthesis of Spirocycles, Carbazoles and Quinolines from Indolyl Ynones.

Authors:  John T R Liddon; Michael J James; Aimee K Clarke; Peter O'Brien; Richard J K Taylor; William P Unsworth
Journal:  Chemistry       Date:  2016-05-19       Impact factor: 5.236

5.  Construction of spirocarbocycles via gold-catalyzed intramolecular dearomatization of naphthols.

Authors:  Wen-Ting Wu; Ren-Qi Xu; Liming Zhang; Shu-Li You
Journal:  Chem Sci       Date:  2016-02-02       Impact factor: 9.825

6.  Modular Synthesis of Polycyclic Alkaloid Scaffolds via an Enantioselective Dearomative Cascade.

Authors:  James A Rossi-Ashton; Aimee K Clarke; Richard J K Taylor; William P Unsworth
Journal:  Org Lett       Date:  2020-01-15       Impact factor: 6.005
  6 in total

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