New paper in J Org Chem

Our latest paper has been published in the Journal of Organic Chemistry. The paper describes a way to make α-substituted vinylsulfonium salts and their application to the synthesis of pyrrolidines fused to either epoxides or cyclopropanes. These heterocycles should be useful building blocks for medicinal chemists. The paper arose from an ongoing collaboration with Prof Varinder Aggarwal at the University of Bristol, and researchers at GlaxoSmithKline. Congratulations to lead author Johnathan Matlock in particular, this is the second publication arising from his ongoing PhD research (supervised by Eoghan and Varinder).

The paper is published online in the Journal of Organic Chemistry and can be accessed at the following link (with a subscription):

J Org Chem 2014 article ASAP. DOI: 10.1021/jo501885z

The research was funded by  EPSRC (Bristol Chemical Synthesis CDT), GSK, SFI and Marie-Curie COFUND.

 

 

Paper published in Chemistry a European Journal

Our latest paper has just appeared online in Chemistry – A European Journal. The paper describes the use of vinylsulfonium salts to synthesise cyclopropane-fused heterocycles from readily available starting materials with excellent levels of diastereoselectivity. These interesting structures should be of particular interest to medicinal chemists. This paper arises from an ongoing collaboration with the Aggarwal group at the University of Bristol, UK. We thank EPSRC, GSK and SFI for funding.

The paper can be read online (with a subscription):

Chem Eur J 2013, early view, doi: 10.1002/chem.201302081

Paper published in Helv. Chim. Acta

Our latest paper was published online in Helvetica Chimica Acta in a special edition in honour of Prof Dieter Seebach’s 75th birthday. The paper describes the use of a new chiral vinylsulfonium salt for the synthesis of epoxide and aziridine-fused heterocycles. The method was applied to a synthesis of the core of the mitomycin class of antibiotics. This work was carried out in collaboration with Prof Varinder Aggarwal, Sven Fritz, Zulfiquar Ali and Dr Matt Unthank at the University of Bristol.

We thank EPSRC and the Higher Education Commission of Pakistan for funding.

The paper can be read (with a subscription) at the following link:

Helv. Chim. Acta 2012, 95, 2384; DOI: 10.1002/hlca.201200455

Paper published online in Organic Letters

Our latest paper was published online in Organic Lettters as an ‘as soon as possible’ article. The paper describes the use of trifluoromethyl-substituted vinylsulfonium salts for the synthesis of saturated heterocycles containing the CF₃ group. The epoxide-fused heterocycles are expected to be of interest to medicinal chemists in particular. This work was carried out in collaboration with Prof Varinder Aggarwal, Sven Fritz and Tom West at the University of Bristol. We thank EPSRC and SFI for funding.

The paper can be read (with a subscription) at the following link:

Organic Letters 2012, asap; DOI: 10.1021/ol303200n

Don’t have a subscription? email Eoghan for an electronic preprint:

(eoghan_dot_mcgarrigle_at_ucd_dot_ie).

Azetidine paper published in Synthesis

Our latest paper has been published online in Synthesis. The article describes a new method for the synthesis of azetidines using bromoethyldiphenylsulfonium triflate. Azetidines are attracting a lot of attention from medicinal chemists at the moment.

Synthesis 2012, e-first. Sven P. Fritz, Juan F. Moya, Matthew G. Unthank, Eoghan M. McGarrigle*, Varinder K. Aggarwal* — ‘An Efficient Synthesis of Azetidines with (2-Bromoethyl)sulfonium Triflate.’ DOI: 10.1055/s-0031-1290951

Congratulations to the whole team involved in this paper. Pictured is Sven who bought the drinks for the lab party to celebrate this publication!

Our Article on Bromoethyldiphenylsulfonium triflate goes live.

Our latest article on bromoethyldiphenylsulfonium triflate has been published online in the Encyclopedia of Reagents for Organic Synthesis. The article reviews the use of this reagent and related reagents in synthesis, including (but not limited to) our own contributions.

Encyclopedia of Reagents for Organic Synthesis; Ed. Paquette, L.A.; Crich, D.; Fuchs, P. L.; Molander, G. A.; John Wiley & Sons Ltd.; M. Yar, E. M. McGarrigle, V. K. Aggarwal — ‘Sulfonium, Ethenyldiphenyl-, 1,1,1-Trifluoromethanesulfonate’, eEROS (2012). DOI: 10.1002/047084289X.rn01409

Pictured are Varinder Aggarwal and Muhammad Yar.