Beilstein J. Org. Chem.2025,21, 947–954, doi:10.3762/bjoc.21.78
Abstract We present the first examples of alkene amino-sulfonoxylation reactions that leverage the unique reactivity of carbamate tethered N-alkoxy nitrenium ions. In almost all cases examined, the reactions deliver product with exquisite regioselectivity and diastereoselectivity. The protocols followed
: alkene; amino-sulfonoxylation; metal-free; tethered nitrenium; Introduction
Our laboratory has a programmatic focus on the development of metal-free oxidation reactions that avoid the use of toxic reagents such as osmium and chromium [1][2][3]. In line with this agenda, we recently explored a mild amino
examples of alkene amino-hydroxylation reactions mediated by N-alkoxy nitreniums deliver amino-trifluoroacetate products (Scheme 1) [6]. Here, we describe the first examples of amino-sulfonoxylation reactions of alkenes, which make use of carbamate tethered N-alkoxy nitrenium ions.
Results and Discussion
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Graphical Abstract
Scheme 1:
Existing reports of intramolecular alkene functionalization reactions with nitreniums have focused ...