Alexander P. Pulis

University of Leicester

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Co-Authors

David J. Procter

University of Manchester

Fabien J. T. Talbot

University of Manchester

Varinder K. Aggarwal

University of Bristol

José A. Fernández‐Salas

Universidad Autónoma de Madrid

K-

K. -S. Yeung

University of Bristol

Gregory J. P. Perry

Kyoto University

Gareth P. Howell

AstraZeneca (United Kingdom)

Zhen He

Southern University of Science and Technology

Kevin Yang

University of California, Irvine

Harry J. Shrives

University of Hertfordshire

Cooperative Institutions

University of Manchester

University of Bristol

University of Leicester

AstraZeneca (United Kingdom)

At Bristol

Centre National de la Recherche Scientifique

GlaxoSmithKline (United Kingdom)

Université Laval

Département de Chimie Moléculaire

Cardiff University

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Synthesis of C2 Substituted Benzothiophenes via an Interrupted Pummerer/[3,3]‐Sigmatropic/1,2‐Migration Cascade of Benzothiophene S‐Oxides

Angewandte Chemie International Edition (2018)

Zhen He Harry J. Shrives José A. Fernández‐Salas Alberto Abengózar Jessica Neufeld

Functionalized benzothiophenes are important scaffolds found in molecules with wide ranging biological activity and in organic materials. We describe an efficient, metal-free synthesis of C2 arylated, allylated, and propargylated benzothiophenes. The reaction utilizes synthetically unexplored yet readily accessible benzothiophene S-oxides and phenols, allyl-, or propargyl silanes in a unique cascade sequence. An interrupted Pummerer reaction between benzothiophene S-oxides and the coupling partners yields sulfonium salts that lack aromaticity and therefore allow facile [3,3]-sigmatropic rearrangement. The subsequently generated benzothiophenium salts undergo a previously unexplored 1,2-migration to access C2 functionalized benzothiophenes.

Benzothiophene

Sulfonium

Benzonitrile

10.1002/anie.201801982

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Citations (93)

Enantioselective Generation of Adjacent Stereocenters in a Copper‐Catalyzed Three‐Component Coupling of Imines, Allenes, and Diboranes

Angewandte Chemie International Edition (2016)

K. -S. Yeung Rebecca E. Ruscoe James Rae Alexander P. Pulis David J. Procter

Abstract A highly enantio‐ and diastereoselective copper‐catalyzed three‐component coupling affords the first general synthesis of homoallylic amines bearing adjacent stereocenters from achiral starting materials. The method utilizes a commercially available NHC ligand and copper source, operates at ambient temperature, couples readily available simple imines, allenes, and diboranes, and yields high‐value homoallylic amines that exhibit versatile amino, alkenyl, and boryl units.

Stereocenter

Component (thermodynamics)

10.1002/anie.201606710

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Citations (139)

CCDC 1914139: Experimental Crystal Structure Determination

The Cambridge Structural Database (2020)

Tao Jia Marshall J. Smith Alexander P. Pulis Gregory J. P. Perry David J. Procter

10.5517/ccdc.csd.cc227tfl

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The Interrupted Pummerer Reaction in a Sulfoxide‐Catalyzed Oxidative Coupling of 2‐Naphthols

Angewandte Chemie International Edition (2019)

Zhen He Alexander P. Pulis David J. Procter

A benzothiophene S-oxide catalyst, generated in situ by sulfur oxidation with H2 O2 , mediates the oxidative coupling of 2-naphthols. Key to the catalytic process is the capture and inversion of reactivity of a 2-naphthol partner, using an interrupted Pummerer reaction of an unusual benzothiophene S-oxide, followed by subsequent coupling with a second partner. The new catalytic manifold has been showcased in the synthesis of the bioactive natural products, (±)-nigerone and (±)-isonigerone. Although Pummerer reactions are used widely, their application in catalysis is rare, and our approach represents a new catalytic manifold for metal-free C-C bond formation.

Benzothiophene

Sulfoxide

Pummerer rearrangement

Reactivity

10.1002/anie.201903492

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Citations (41)

CCDC 1864386: Experimental Crystal Structure Determination

The Cambridge Structural Database (2019)

Zhen He Alexander P. Pulis David J. Procter

10.5517/ccdc.csd.cc20l1h5

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Citations (0)

CCDC 1934977: Experimental Crystal Structure Determination

The Cambridge Structural Database (2019)

Jiajie Yan Alexander P. Pulis Gregory J. P. Perry David J. Procter

10.5517/ccdc.csd.cc22yhm5

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CCDC 1872999: Experimental Crystal Structure Determination

The Cambridge Structural Database (2018)

Kevin Yang Alexander P. Pulis Gregory J. P. Perry David J. Procter

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc20w0b8

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CCDC 1871096: Experimental Crystal Structure Determination

The Cambridge Structural Database (2019)

K. -S. Yeung Fabien J. T. Talbot Gareth P. Howell Alexander P. Pulis David J. Procter

10.5517/ccdc.csd.cc20t0yt

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Citations (0)

Correction to Synthesis of Enantioenriched Tertiary Boronic Esters from Secondary Allylic Carbamates. Application to the Synthesis of C30 Botryococcene

Journal of the American Chemical Society (2012)

Alexander P. Pulis Varinder K. Aggarwal

ADVERTISEMENT RETURN TO ISSUEPREVAddition/CorrectionORIGINAL ARTICLEThis notice is a correctionCorrection to Synthesis of Enantioenriched Tertiary Boronic Esters from Secondary Allylic Carbamates. Application to the Synthesis of C30 BotryococceneAlexander P. Pulis and Varinder K. Aggarwal*Cite this: J. Am. Chem. Soc. 2012, 134, 27, 11298Publication Date (Web):June 26, 2012Publication History Published online26 June 2012Published inissue 11 July 2012https://pubs.acs.org/doi/10.1021/ja304872jhttps://doi.org/10.1021/ja304872jcorrectionACS PublicationsCopyright © 2012 American Chemical Society. This publication is available under these Terms of Use. Request reuse permissions This publication is free to access through this site. Learn MoreArticle Views2996Altmetric-Citations1LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail PDF (120 KB) Get e-AlertscloseSupporting Info (1)»Supporting Information Supporting Information Get e-Alerts

Boronic acid

10.1021/ja304872j

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Citations (2)

CCDC 1871102: Experimental Crystal Structure Determination

The Cambridge Structural Database (2019)

K. -S. Yeung Fabien J. T. Talbot Gareth P. Howell Alexander P. Pulis David J. Procter

10.5517/ccdc.csd.cc20t141

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Citations (0)