Organic Letters
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Scheme 5. Proposed Mechanism for the Intermolecular
Amidoselenenylation of Alkenes and N-
Phenylseleno)phthalimidea,b
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reaction at room temperature affords the thermodynamically
more stable Markovnikov adducts.
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In conclusion, we have developed a catalytic, simple, efficient,
atom-economic, and regioselective and diastereoselective
amidoselenenylation reaction of electron-rich alkenes using
N-(phenylseleno)phthalimide as both a nitrogen and selenium
source. The use of phthalimide-type electrophilic selenium
reagents is also synthetically appealing because such an N-
protection moiety can be readily removed for subsequent
transformations. Investigations of the enantioselective amido-
selenenylation reaction are currently ongoing.
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ASSOCIATED CONTENT
Supporting Information
■
*
S
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Experimental procedures and H NMR and 13C NMR
spectral data for compounds 3, 4a, 5a, 5a′, 5c, 5s, and 9a,
HSQC and HMBC spectral data for compound 3r,
crystal data of compound 3o, and ROESY spectra for
1
(
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AUTHOR INFORMATION
■
*
2
756.
8) Tiecco, M.; Testaferri, L.; Santi, C.; Tomassini, C.; Marini, F.;
Bagnoli, L.; Temperini, A. Angew. Chem., Int. Ed. 2003, 42, 3131.
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(
Notes
́
The authors declare no competing financial interest.
(
W. Synlett 2012, 23, 907. (c) Huang, X.; Tang, E.; Xu, W. M.; Cao, J. J.
Comb. Chem. 2005, 7, 802. (d) Xu, W. M.; Xu; Huang, X.; Tang, E. J.
Comb. Chem. 2005, 7, 726. (e) Tang, E.; Huang, X.; Xu, W. M.
Tetrahedron 2004, 60, 9963. (f) Tang, E.; Mao, D. S.; Li, W.; Gao, Z.
Y.; Yao, P. F. Heterocycles 2012, 85, 667. (g) Tang, E.; Li, W.; Gao, Z.
Y.; Gu, X. Chin. Chem. Lett. 2012, 23, 631.
ACKNOWLEDGMENTS
■
This work was supported by the Ministry of Education of the
People’s Republic of China (Program for Changjiang Scholars
and Innovative Research Team in University, IRT13095) and
the Natural Science Foundation of China (NSFC 21162032).
(11) Nicolaou, K. C.; Petasis, N. A.; Claremon, D. A. Tetrahedron
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985, 41, 4835.
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