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:
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(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 e...
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- Publication status:
- Published
- Peer review status:
- Peer reviewed
- Version:
- Publisher's version
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- Files:
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(pdf, 1.5MB)
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- Publisher copy:
- 10.1021/acs.joc.5b01804
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Authors
Funding
+ Engineering and Physical Sciences Research Council
More from this funder
Funding agency for:
Jackson, KE
Bibliographic Details
- Publisher:
- American Chemical Society Publisher's website
- Journal:
- The Journal of organic chemistry Journal website
- Volume:
- 80
- Issue:
- 20
- Pages:
- 9838-9846
- Publication date:
- 2015-10-05
- DOI:
- EISSN:
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1520-6904
- ISSN:
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0022-3263
- URN:
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uuid:c4e0092f-03a3-4f3a-bceb-df65167a184b
- Source identifiers:
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572928
- Local pid:
- pubs:572928
Item Description
- Language:
- English
Terms of use
- Copyright holder:
- American Chemical Society
- Copyright date:
- 2015
- Notes:
- 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.
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