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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 e...

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Publication status:
Published
Peer review status:
Peer reviewed
Version:
Publisher's version

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Publisher copy:
10.1021/acs.joc.5b01804

Authors


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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Mortimer, CL More by this author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
McKenna, JM More by this author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
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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:
1520-6904
ISSN:
0022-3263
URN:
uuid:c4e0092f-03a3-4f3a-bceb-df65167a184b
Source identifiers:
572928
Local pid:
pubs:572928
Language:
English

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