Transformation of Linear Alkenyl <i>N</i>-Alkoxy Carbamates into Cyclic Bromo Carbonates

We present a protocol for the facile conversion of linear alkenyl <i>N</i>-alkoxy carbamates into cyclic bromo carbonates. The reaction is operationally simple, uses widely available, inexpensive reagents, and requires no rigorous exclusion of air or moisture. A range of functional group...

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Main Authors: Shyam Sathyamoorthi, Steven P. Kelley
Format: Article
Language:English
Published: MDPI AG 2025-06-01
Series:Chemistry
Subjects:
Online Access:https://www.mdpi.com/2624-8549/7/3/99
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author Shyam Sathyamoorthi
Steven P. Kelley
author_facet Shyam Sathyamoorthi
Steven P. Kelley
author_sort Shyam Sathyamoorthi
collection DOAJ
description We present a protocol for the facile conversion of linear alkenyl <i>N</i>-alkoxy carbamates into cyclic bromo carbonates. The reaction is operationally simple, uses widely available, inexpensive reagents, and requires no rigorous exclusion of air or moisture. A range of functional groups is compatible, and the reaction diastereoselectivities vary from good to excellent. The reactions are scalable, and the resultant carbonates can be further transformed.
format Article
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institution OA Journals
issn 2624-8549
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publishDate 2025-06-01
publisher MDPI AG
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spelling doaj-art-b4fb3c9b8c8f4151bfa35687c2bca2192025-08-20T02:24:19ZengMDPI AGChemistry2624-85492025-06-01739910.3390/chemistry7030099Transformation of Linear Alkenyl <i>N</i>-Alkoxy Carbamates into Cyclic Bromo CarbonatesShyam Sathyamoorthi0Steven P. Kelley1Department of Medicinal Chemistry, University of Kansas, Lawrence, KS 66047, USADepartment of Chemistry, University of Missouri—Columbia, Columbia, MO 65211, USAWe present a protocol for the facile conversion of linear alkenyl <i>N</i>-alkoxy carbamates into cyclic bromo carbonates. The reaction is operationally simple, uses widely available, inexpensive reagents, and requires no rigorous exclusion of air or moisture. A range of functional groups is compatible, and the reaction diastereoselectivities vary from good to excellent. The reactions are scalable, and the resultant carbonates can be further transformed.https://www.mdpi.com/2624-8549/7/3/99heterocyclesalkenesbrominationcarbonatestethered functionalization
spellingShingle Shyam Sathyamoorthi
Steven P. Kelley
Transformation of Linear Alkenyl <i>N</i>-Alkoxy Carbamates into Cyclic Bromo Carbonates
Chemistry
heterocycles
alkenes
bromination
carbonates
tethered functionalization
title Transformation of Linear Alkenyl <i>N</i>-Alkoxy Carbamates into Cyclic Bromo Carbonates
title_full Transformation of Linear Alkenyl <i>N</i>-Alkoxy Carbamates into Cyclic Bromo Carbonates
title_fullStr Transformation of Linear Alkenyl <i>N</i>-Alkoxy Carbamates into Cyclic Bromo Carbonates
title_full_unstemmed Transformation of Linear Alkenyl <i>N</i>-Alkoxy Carbamates into Cyclic Bromo Carbonates
title_short Transformation of Linear Alkenyl <i>N</i>-Alkoxy Carbamates into Cyclic Bromo Carbonates
title_sort transformation of linear alkenyl i n i alkoxy carbamates into cyclic bromo carbonates
topic heterocycles
alkenes
bromination
carbonates
tethered functionalization
url https://www.mdpi.com/2624-8549/7/3/99
work_keys_str_mv AT shyamsathyamoorthi transformationoflinearalkenylinialkoxycarbamatesintocyclicbromocarbonates
AT stevenpkelley transformationoflinearalkenylinialkoxycarbamatesintocyclicbromocarbonates