Stereospecific SuFEx Reactivity of Highly Enantioenriched Sulfondiimidoyl Fluorides

Abstract

Sulfondiimidoyl fluorides are established SuFEx platforms, yet their potential in asymmetric synthesis remains largely unexplored. Herein we report stereospecific SuFEx transformations of highly enantioenriched sulfondiimidoyl fluorides to access sulfone diimines, sulfondiimidamides and sulfondiimidates with complete chirality transfer. For sulfone diimine formation, heteroleptic triorganozincates serve as mild and chemoselective carbon nucleophiles, enabling exclusive stereospecific allyl and benzyl transfer with broad functional group tolerance. The accomplished orthogonal deprotection of sulfondiimidoyl scaffolds demonstrates their additional synthetic flexibility. Collectively, this work establishes sulfondiimidoyl fluorides as robust chiral SuFEx building blocks for asymmetric synthesis.