Synthesis of sulfoximine propargyl carbamates under improved conditions for rhodium catalyzed carbamate transfer to sulfoxides
File(s)MS sulfoximine propargyl carbamates revised.pdf (914.47 KB)
Accepted version
Author(s)
Zhong, Zhenhao
Chesti, Julian
Armstrong, Alan
Bull, James
Type
Journal Article
Abstract
Sulfoximines provide aza-analogues of sulfones, with potentially improved properties for medicinal chemistry. The sulfoximine nitrogen also provides an additional vector for the inclusion of other functionality. Here, we report improved conditions for rhodium catalyzed synthesis of sulfoximine (and sulfilimine) carbamates, especially for previously low-yielding carbamates containing pi-functionality. Notably we report the preparation of propargyl sulfoximine carbamates to provide an alkyne as a potential click handle. Using Rh2(esp)2 as catalyst and a DOE optimization approach provided considerably increased yields.
Date Issued
2022-12-02
Date Acceptance
2022-11-03
Citation
The Journal of Organic Chemistry, 2022, 87 (23), pp.16115-16126
ISSN
0022-3263
Publisher
American Chemical Society
Start Page
16115
End Page
16126
Journal / Book Title
The Journal of Organic Chemistry
Volume
87
Issue
23
Copyright Statement
© 2022 The Authors. Published by American Chemical Society. This work is licensed under a Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0/).
License URL
Publication Status
Published
Date Publish Online
2022-11-15