Organic Letters
Letter
In summary, both α-(2-pyridyl) and α-(3-pyridyl) alkylamines
may be arylated with total enantiospecificity at their α-position by
intramolecular migration of an aryl substituent within their
lithiated N′-aryl urea derivatives. Despite their delocalized
structure, the intermediate 2-pyridyl-substituted anions are
configurational stable on the time scale of the rearrangement.
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ASSOCIATED CONTENT
Supporting Information
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S
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Oxford, 2002.
Crystallographic data for (R)-11c (CIF)
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AUTHOR INFORMATION
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(13) Prasad, K. R.; Revu, O. Tetrahedron 2013, 69, 8422.
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ORCID
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Tetrahedron: Asymmetry 2006, 17, 3163.
(16) Fournier, A. M.; Brown, R. A.; Farnaby, W.; Miyatake-Ondozabal,
Author Contributions
H.; Clayden, J. Org. Lett. 2010, 12, 2222.
(17) Zimmerman, H. E.; Singer, L.; Thyagarajan, B. S. J. Am. Chem. Soc.
§J.M. and W.Z. contributed equally.
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959, 81, 108.
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Notes
The authors declare no competing financial interest.
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ACKNOWLEDGMENTS
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This work was supported by the EU (Marie Curie IEF ENOLAR)
and by the BBSRC. We thank Dr. James Raftery (University of
Manchester) for determining the X-ray crystal structure of (R)-
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Organometallics 1993, 12, 1201.
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11c.
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23) Theerofamines 16a-f, likethose of12b,dwas notdetermined, but
was assumed to be the same as the parent urea.
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