Journal article
α- and α'-lithiation-electrophile trapping of N-thiopivaloyl and N-tert-butoxythiocarbonyl α-substituted azetidines: rationalization of the regiodivergence using NMR and computation
- Abstract:
- (1)H NMR and computational analyses provide insight into the regiodivergent (α- and α'-) lithiation-electrophile trapping of N-thiopivaloyl- and N-(tert-butoxythiocarbonyl)-α-alkylazetidines. The magnitudes of the rotation barriers in these azetidines indicate that rotamer interconversions do not occur at the temperature and on the time scale of the lithiations. The NMR and computational studies support the origin of regioselectivity as being thiocarbonyl-directed lithiation from the lowest energy amide-like rotameric forms (cis for N-thiopivaloyl and trans for N-tert-butoxythiocarbonyl).
- Publication status:
- Published
- Peer review status:
- Peer reviewed
Actions
Access Document
- Files:
-
-
(Preview, Version of record, pdf, 1.5MB, Terms of use)
-
(Preview, Supplementary materials, pdf, 3.0MB, Terms of use)
-
- Publisher copy:
- 10.1021/acs.joc.5b01804
Authors
+ Engineering and Physical Sciences Research Council
More from this funder
- Funding agency for:
- Jackson, KE
- Publisher:
- American Chemical Society
- Journal:
- Journal of organic chemistry More from this journal
- Volume:
- 80
- Issue:
- 20
- Pages:
- 9838-9846
- Publication date:
- 2015-09-24
- DOI:
- EISSN:
-
1520-6904
- ISSN:
-
0022-3263
- Language:
-
English
- Pubs id:
-
pubs:572928
- UUID:
-
uuid:c4e0092f-03a3-4f3a-bceb-df65167a184b
- Local pid:
-
pubs:572928
- Source identifiers:
-
572928
- Deposit date:
-
2016-03-09
Terms of use
- Copyright holder:
- American Chemical Society
- Copyright date:
- 2015
- Rights statement:
- Copyright © 2015 American Chemical Society. 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.
- Licence:
- CC Attribution (CC BY)
If you are the owner of this record, you can report an update to it here: Report update to this record