29723-63-5Relevant academic research and scientific papers
Synthesis of NH-sulfoximines from sulfides by chemoselective one-pot N- and O-transfers
Tota, Arianna,Zenzola, Marina,Chawner, Stephen J.,John-Campbell, Sahra St,Carlucci, Claudia,Romanazzi, Giuseppe,Degennaro, Leonardo,Bull, James A.,Luisi, Renzo
, p. 348 - 351 (2017)
Direct synthesis of NH-sulfoximines from sulfides has been achieved through O and NH transfer in the same reaction, occurring with complete selectivity. The reaction is mediated by bisacetoxyiodobenzene under simple conditions and employs inexpensive N-so
Straightforward Strategies for the Preparation of NH-Sulfox-imines: A Serendipitous Story
Bull, James A.,Degennaro, Leonardo,Luisi, Renzo
, p. 2525 - 2538 (2017/11/28)
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.
Copper promoted: N -alkylation of sulfoximines with alkylboronic acid under mild conditions
Gupta, Surabhi,Chaudhary, Priyanka,Muniyappan, Nalluchamy,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
supporting information, p. 8493 - 8498 (2017/10/27)
The copper meditated N-methylation of sulfoximines using methylboronic acid is reported. The reactions provide excellent yields in a short span of time under mild conditions. The optimized conditions were also found to be suitable for the N-alkylation of sulfoximine with different alkylboronic acids. In addition, N-methylation and cyclopropylation of the bioactive l-methionine sulfoximine derivative was demonstrated under standard reaction conditions.
