Synlett
DOI: 10.1055/s-0036-1590874
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© Georg Thieme Verlag Stuttgart · New York

Straightforward Strategies for the Preparation of NH-Sulfox­imines: A Serendipitous Story

James A. Bull*a, Leonardo Degennarob, Renzo Luisi*b
  • aDepartment of Chemistry, Imperial College London, South Kensington, London, SW7 2AZ, UK   Email: j.bull@imperial.ac.uk
  • bDepartment of Pharmacy — Drug Sciences, University of Bari “A. Moro”, Via E. Orabona 4, Bari 70125, Italy   Email: renzo.luisi@uniba.it
Further Information

Publication History

Received: 31 May 2017

Accepted after revision: 18 July 2017

Publication Date:
05 September 2017 (eFirst)

Abstract

Sulfoximines are emerging as valuable new isosteres for use in medicinal chemistry, with the potential to modulate physicochemical properties. Recent developments in synthetic strategies have made the unprotected ‘free’ NH-sulfoximine group more readily available, facilitating further study. This account reviews approaches to NH-sulfoximines, with a focus on our contribution to the field. Starting from the development of catalytic strategies involving transition metals, more sustainable metal-free processes have been discovered. In particular, the use of hypervalent iodine reagents to mediate NH-transfer to sulfoxides is described, along with an assessment of the substrate scope. Furthermore, a one-pot strategy to convert sulfides directly into NH-sulfoximines is discussed, with N- and O-transfer occurring under the reaction conditions. Mechanistic evidence for the new procedures is included as well as relevant synthetic applications that further exemplify the potential of these approaches.

1 Introduction

2 Strategies to Form NH-Sulfoximines Involving Transition-Metal Catalysts

3 Metal-Free Strategies to Prepare NH-Sulfoximines

4 Mechanistic Evidence for the Direct Synthesis of NH-Sulfoximines from Sulfoxides and Sulfides

5 Further Applications

6 Conclusion