Catalyst-driven scaffold diversity: selective synthesis of spirocycles, carbazoles and quinolines from indolyl ynones

John T R Liddon; Michael J. James; Aimee K. Clarke; Peter O'Brien; Richard J K Taylor; William P. Unsworth

doi:10.1002/chem.201601836

Catalyst-driven scaffold diversity: selective synthesis of spirocycles, carbazoles and quinolines from indolyl ynones

John T R Liddon, Michael J. James, Aimee K. Clarke, Peter O'Brien, Richard J K Taylor^*, William P. Unsworth

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Medicinally relevant spirocyclic indolenines, carbazoles and quinolines can each be directly synthesised selectively from common indolyl ynone starting materials by catalyst variation. The high yielding, divergent reactions all proceed via an initial dearomatising spirocyclisation reaction to generate an intermediate vinyl metal species which then rearranges selectively by careful choice of catalyst and reaction conditions.

Original language	English
Pages (from-to)	8777–8780
Number of pages	4
Journal	Chemistry : A European Journal
Volume	22
Issue number	26
Early online date	19 May 2016
DOIs	https://doi.org/10.1002/chem.201601836
Publication status	Published - 20 Jun 2016

Bibliographical note

© 2016, The publisher. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details

Keywords

carbazoles
catalysis
diversity
quinolines
spirocycles
Stereoisomerism
Spiro Compounds/chemical synthesis
Indoles/chemistry
Carbazoles/chemical synthesis
Catalysis
Mesylates/chemistry
Quinolines/chemical synthesis

Access to Document

10.1002/chem.201601836Licence: CC BY

John Liddon paper version 8- revised for transfer to CEJ
© 2016, The publisher. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details
Submitted manuscript, 721 KB
Liddon_et_al-2016-Chemistry_-_A_European_Journal
© 2016, The publisher. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details
Accepted author manuscript, 1.05 MB

Cite this

@article{6ee5d52513134c5e997c9ed6a693f8c9,

title = "Catalyst-driven scaffold diversity: selective synthesis of spirocycles, carbazoles and quinolines from indolyl ynones",

abstract = "Medicinally relevant spirocyclic indolenines, carbazoles and quinolines can each be directly synthesised selectively from common indolyl ynone starting materials by catalyst variation. The high yielding, divergent reactions all proceed via an initial dearomatising spirocyclisation reaction to generate an intermediate vinyl metal species which then rearranges selectively by careful choice of catalyst and reaction conditions.",

keywords = "carbazoles, catalysis, diversity, quinolines, spirocycles, Stereoisomerism, Spiro Compounds/chemical synthesis, Indoles/chemistry, Carbazoles/chemical synthesis, Catalysis, Mesylates/chemistry, Quinolines/chemical synthesis",

author = "Liddon, {John T R} and James, {Michael J.} and Clarke, {Aimee K.} and Peter O'Brien and Taylor, {Richard J K} and Unsworth, {William P.}",

note = "{\textcopyright} 2016, The publisher. This is an author-produced version of the published paper. Uploaded in accordance with the publisher{\textquoteright}s self-archiving policy. Further copying may not be permitted; contact the publisher for details",

year = "2016",

month = jun,

day = "20",

doi = "10.1002/chem.201601836",

language = "English",

volume = "22",

pages = "8777–8780",

journal = "Chemistry : A European Journal",

issn = "0947-6539",

publisher = "Wiley-Blackwell",

number = "26",

}

TY - JOUR

T1 - Catalyst-driven scaffold diversity

T2 - selective synthesis of spirocycles, carbazoles and quinolines from indolyl ynones

AU - Liddon, John T R

AU - James, Michael J.

AU - Clarke, Aimee K.

AU - O'Brien, Peter

AU - Taylor, Richard J K

AU - Unsworth, William P.

N1 - © 2016, The publisher. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details

PY - 2016/6/20

Y1 - 2016/6/20

N2 - Medicinally relevant spirocyclic indolenines, carbazoles and quinolines can each be directly synthesised selectively from common indolyl ynone starting materials by catalyst variation. The high yielding, divergent reactions all proceed via an initial dearomatising spirocyclisation reaction to generate an intermediate vinyl metal species which then rearranges selectively by careful choice of catalyst and reaction conditions.

AB - Medicinally relevant spirocyclic indolenines, carbazoles and quinolines can each be directly synthesised selectively from common indolyl ynone starting materials by catalyst variation. The high yielding, divergent reactions all proceed via an initial dearomatising spirocyclisation reaction to generate an intermediate vinyl metal species which then rearranges selectively by careful choice of catalyst and reaction conditions.

KW - carbazoles

KW - catalysis

KW - diversity

KW - quinolines

KW - spirocycles

KW - Stereoisomerism

KW - Spiro Compounds/chemical synthesis

KW - Indoles/chemistry

KW - Carbazoles/chemical synthesis

KW - Catalysis

KW - Mesylates/chemistry

KW - Quinolines/chemical synthesis

UR - http://www.scopus.com/inward/record.url?scp=84971013149&partnerID=8YFLogxK

U2 - 10.1002/chem.201601836

DO - 10.1002/chem.201601836

M3 - Article

C2 - 27124236

SN - 0947-6539

VL - 22

SP - 8777

EP - 8780

JO - Chemistry : A European Journal

JF - Chemistry : A European Journal

IS - 26

ER -

Catalyst-driven scaffold diversity: selective synthesis of spirocycles, carbazoles and quinolines from indolyl ynones

Abstract

Bibliographical note

Keywords

Access to Document

Other files and links

Peter Andrew O'Brien

Richard John Kenneth Taylor

William Paul Unsworth

Catalytic Asymmetric Dearomative Spirocyclisations

Raw data for the paper 'Catalyst-Driven Scaffold Diversity: Selective Synthesis of Spirocycles, Carbazoles and Quinolines from Indolyl Ynones'

Cite this

Catalyst-driven scaffold diversity: selective synthesis of spirocycles, carbazoles and quinolines from indolyl ynones

Abstract

Bibliographical note

Keywords

Access to Document

Other files and links

Profiles

Peter Andrew O'Brien

Richard John Kenneth Taylor

William Paul Unsworth

Projects

Catalytic Asymmetric Dearomative Spirocyclisations

Datasets

Raw data for the paper 'Catalyst-Driven Scaffold Diversity: Selective Synthesis of Spirocycles, Carbazoles and Quinolines from Indolyl Ynones'

Cite this