Journal of the American Chemical Society
Communication
(13) Smith, M. B. March’s Advanced Organic Chemistry: Reactions,
Mechanisms, and Structure, 7th ed.; Wiley: Hoboken, NJ, 2013.
(14) Hartwig, J. F. Organotransition Metal Chemistry: From Bonding to
Catalysis; University Science Books: Sausalito, CA, 2010.
(15) See the Supporting Information.
ASSOCIATED CONTENT
* Supporting Information
Experimental procedures and spectra. This material is available
■
S
(16) Substitution at the γ-position on the allyl group led to either no
reaction or products resulting from olefin isomerization and enamine−
amine exchange.
AUTHOR INFORMATION
Corresponding Author
■
(17) Diastereoselectivities were determined by analysis of the crude
1H NMR spectra.
Author Contributions
(18) The relative stereochemistry was established by comparison to
the reported 1H NMR shifts for 14a. See: Xie, J.-H.; Liu, S.; Kong, W.-
L.; Bai, W.-J.; Wang, A. C.; Wang, L.-X.; Zhou, Q.-L. J. Am. Chem. Soc.
2009, 131, 4222.
(19) (a) Julian, L. D.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132,
13813. (b) Hesp, K. D.; Tobisch, S.; Stradiotto, M. J. Am. Chem. Soc.
2010, 132, 413. (c) Liu, Z.; Yamamichi, H.; Madrahimov, S. T.;
Hartwig, J. F. J. Am. Chem. Soc. 2011, 133, 2772−2782.
†A.R.I. and S.C.E. contributed equally.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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This work was generously supported by the University of
Illinois. The authors acknowledge J. Wang, J. Brewster, and L.
Weir for assistance in substrate synthesis and Prof. Scott E.
Denmark for helpful discussions.
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