Strain-release driven reactivity of a chiral SuFEx reagent provides stereocontrolled access to sulfinamides, sulfonimidamides, and sulfoximines

Paresh R. Athawale, Zachary P. Shultz, Alexandra Saputo, Yvonne D. Hall and Justin M. Lopchuk ()
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Paresh R. Athawale: 12902 Magnolia Drive
Zachary P. Shultz: 12902 Magnolia Drive
Alexandra Saputo: University of South Florida
Yvonne D. Hall: 12902 Magnolia Drive
Justin M. Lopchuk: 12902 Magnolia Drive

Nature Communications, 2024, vol. 15, issue 1, 1-12

Abstract: Abstract Efforts aimed at enriching the chemical and structural diversity of small molecules have invigorated synthetic exploration in the last two decades. Spatially defined molecular functionality serves as the foundation to construct unique chemical space to further advance discovery science. The chiral SuFEx reagent t-BuSF provides a modular platform for the stereocontrolled bifunctionalization of sulfur. Here we report a third functional feature of t-BuSF enabled by carbamoyl torsional strain-release that further expands the S(IV) and S(VI) chemical space accessible as showcased in over seventy examples, multiple applications in medicinal chemistry, organocatalysis, and diversity-oriented synthesis. The methods presented herein allow for rapid asymmetric diversification around a stereodefined sulfur center with readily available building blocks, improving upon the current state-of-the-art for sulfinyl and sulfonimidoyl synthesis.

Date: 2024
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DOI: 10.1038/s41467-024-51224-w

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