Synthesis of Sulfoximine Carbamates by Rhodium-Catalyzed Nitrene Transfer of Carbamates to Sulfoxides
File(s)
Accepted version
Published version
Author(s)
Zenzola, M
Doran, R
Luisi, R
Bull, JA
Type
Journal Article
Abstract
Sulfoximines are of considerable interest for incorporation into medicinal compounds. A convenient synthesis of N-protected sulfoximines is achieved, under mild conditions, by rhodium-catalyzed transfer of carbamates to sulfoxides. The first examples of 4-membered thietane-oximines are prepared. Sulfoximines bearing Boc and Cbz groups are stable to further cross coupling reactions, and readily deprotected. This method may facilitate the preparation of NH-sulfoximines providing improved (global) deprotection strategies, which is illustrated in the synthesis of methionine sulfoxide (MSO).
Date Issued
2015-06-02
Date Acceptance
2015-05-20
Citation
Journal of Organic Chemistry, 2015, 80 (12), pp.6391-6399
ISSN
1520-6904
Publisher
American Chemical Society
Start Page
6391
End Page
6399
Journal / Book Title
Journal of Organic Chemistry
Volume
80
Issue
12
Copyright Statement
© 2015 American Chemical Society. ACS AuthorChoice - This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
License URL
Identifier
http://pubs.acs.org/doi/abs/10.1021/acs.joc.5b00844
Publication Status
Published
Publisher URL