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Harnessing tethered nitreniums for diastereoselective amino-sulfonoxylation of alkenes

Shyam Sathyamoorthi, Appasaheb K. Nirpal, Dnyaneshwar A. Gorve and Steven P. Kelley

Beilstein J. Org. Chem. 2025, 21, 947–954. https://doi.org/10.3762/bjoc.21.78

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Harnessing tethered nitreniums for diastereoselective amino-sulfonoxylation of alkenes

Shyam Sathyamoorthi, Appasaheb K. Nirpal, Dnyaneshwar A. Gorve and Steven P. Kelley

Beilstein J. Org. Chem. 2025, 21, 947–954. https://doi.org/10.3762/bjoc.21.78

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Sathyamoorthi, S.; Nirpal, A. K.; Gorve, D. A.; Kelley, S. P. Beilstein J. Org. Chem. 2025, 21, 947–954. doi:10.3762/bjoc.21.78

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TY  - JOUR
A1  - Sathyamoorthi, Shyam
A1  - Nirpal, Appasaheb K.
A1  - Gorve, Dnyaneshwar A.
A1  - Kelley, Steven P.
T1  - Harnessing tethered nitreniums for diastereoselective amino-sulfonoxylation of alkenes
JF  - Beilstein Journal of Organic Chemistry
PY  - 2025///
VL  - 21
SP  - 947
EP  - 954
SN  - 1860-5397
DO  - 10.3762/bjoc.21.78
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.21.78
KW  - alkene
KW  - amino-sulfonoxylation
KW  - metal-free
KW  - tethered nitrenium
N2  - 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 are operationally very simple and only use commercial I(III) reagents and sulfonic acids, amounting to a metal-free protocol for alkene amino-oxygenation. No special precautions need be taken to exclude air or ambient moisture, and the products are amenable to further transformations.
ER  -

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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)