Organic Letters
Letter
hydroiodic acid methodology (21) followed by catalytic
hydrogenation (22, Scheme 9).
REFERENCES
■
(1) Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014,
57, 10257.
(2) Nebe, M. M.; Opatz, T. In Advances in Heterocyclic Chemistry;
Scriven, E. F. V., Ramsden, C. A., Eds.; Academic Press: Cambridge,
MA, 2017; Vol. 122, p 191.
Scheme 9. Preparation of a Variety Chiral Secondary
Amines
(3) Dobbs, A. P.; Guesne, S. J. J.; Hursthouse, M. B.; Coles, S. J.
Synlett 2003, 1740.
(4) Dobbs, A. P.; Guesne, S. J. J.; Martinovic, S.; Coles, S. J.;
Hursthouse, M. B. J. Org. Chem. 2003, 68, 7880.
(5) Blumenkopf, T. A.; Overman, L. E. Chem. Rev. 1986, 86, 857.
(6) Overman, L. E.; Malone, T. C.; Meier, G. P. J. Am. Chem. Soc.
1983, 105, 6993.
(7) Overman, L. E.; Burk, R. M. Tetrahedron Lett. 1984, 25, 5739.
(8) Flann, C.; Malone, T. C.; Overman, L. E. J. Am. Chem. Soc. 1987,
109, 6097.
(9) Daub, G. W.; Heerding, D. A.; Overman, L. E. Tetrahedron 1988,
44, 3919.
(10) Castro, P.; Overman, L. E.; Zhang, X. M.; Mariano, P. S.
Tetrahedron Lett. 1993, 34, 5243.
(11) Dobbs, A. P.; Guesne, S. J. Synlett 2005, 2101.
(12) Royer, J.; Bonin, M.; Micouin, L. Chem. Rev. 2004, 104, 2311.
(13) Liu, L. P.; Kaib, P. S. J.; Tap, A.; List, B. J. Am. Chem. Soc. 2016,
138, 10822.
(14) Tsui, G. C.; Liu, L. P.; List, B. Angew. Chem., Int. Ed. 2015, 54,
7703.
In conclusion, we have reported the first examples of an
asymmetric aza-silyl-Prins reaction, giving rise to piperidines
and pipecolic acid derivatives, in high yields and as a single
enantiomer. Applications of the methodology are currently
being investigated and will be reported in due course.
(15) Full details of optimization studies, together with the reagents
(16) Chitsaz, S.; Neumuller, B. Organometallics 2001, 20, 2338.
(17) Desimoni, G.; Faita, G.; Livieri, A.; Mella, M.; Ponta, L.;
Boiocchi, M. Eur. J. Org. Chem. 2012, 2012, 2916.
(18) Desimoni, G.; Faita, G.; Toscanini, M.; Boiocchi, M. Chem. -
Eur. J. 2008, 14, 3630.
(19) Du, P.; Zhou, H. F.; Sui, Y. B.; Liu, Q. X.; Zou, K. Tetrahedron
2016, 72, 1573.
(20) Fu, F.; Teo, Y. C.; Loh, T. P. Tetrahedron Lett. 2006, 47, 4267.
(21) Fukuzawa, S.; Matsuzawa, H.; Metoki, K. Synlett 2001, 2001,
709.
ASSOCIATED CONTENT
* Supporting Information
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S
The Supporting Information is available free of charge on the
Preparation, screening results, characterization data,
(22) Ghosh, R.; Maiti, S. J. Mol. Catal. A: Chem. 2007, 264, 1.
(23) Gutierrez, E. G.; Wong, C. J.; Sahin, A. H.; Franz, A. K. Org.
Lett. 2011, 13, 5754.
Accession Codes
tallographic data for this paper. These data can be obtained
Cambridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
(24) Konczyk, A. A.; Szawkalo, J.; Maurin, J. K.; Czarnocki, Z. Helv.
Chim. Acta 2013, 96, 1348.
(25) Lu, J.; Hong, M. L.; Ji, S. J.; Loh, T. P. Chem. Commun. 2005,
1010.
(26) Lu, J.; Ji, S. J.; Teo, Y. C.; Loh, T. P. Org. Lett. 2005, 7, 159.
(27) Takita, R.; Yakura, K.; Ohshima, T.; Shibasaki, M. J. Am. Chem.
Soc. 2005, 127, 13760.
(28) Teo, Y. C.; Goh, E. L.; Loh, T. P. Tetrahedron Lett. 2005, 46,
6209.
(29) Zhao, B.; Loh, T. P. Org. Lett. 2013, 15, 2914.
(30) Zhao, J. F.; Tan, B. H.; Loh, T. P. Chem. Sci. 2011, 2, 349.
(31) Zhao, J. F.; Tan, B. H.; Zhu, M. K.; Tjan, T. B. W.; Loh, T. P.
Adv. Synth. Catal. 2010, 352, 2085.
AUTHOR INFORMATION
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Corresponding Author
ORCID
(32) Zhao, J. F.; Tsui, H. Y.; Wu, P. J.; Lu, J.; Loh, T. P. J. Am. Chem.
Soc. 2008, 130, 16492.
(33) Teng, T. F.; Lin, J. H.; Yang, T. K. Heterocycles 1990, 31, 1201.
(34) Skiles, J. W.; Giannousis, P. P.; Fales, K. R. Bioorg. Med. Chem.
Lett. 1996, 6, 963.
Notes
The authors declare no competing financial interest.
(35) Golubev, A. S.; Schedel, H.; Radics, G.; Sieler, J.; Burger, K.
Tetrahedron Lett. 2001, 42, 7941.
(36) Jiang, R.; Song, X. Y.; Bali, P.; Smith, A.; Bayona, C. R.; Lin, L.;
Cameron, M. D.; McDonald, P. H.; Kenny, P. J.; Kamenecka, T. M.
Bioorg. Med. Chem. Lett. 2012, 22, 3890.
(37) Agami, C.; Couty, F.; Poursoulis, M.; Vaissermann, J.
Tetrahedron 1992, 48, 431.
(38) Deposited with the Cambridge Crystallographic Data Centre:
CCDC 1867514.
ACKNOWLEDGMENTS
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The authors wish to think the European Union (Marie Curie
Individual Fellowship to R.R.M.), EPSRC (studentship to
S.J.J.G.) and GlaxoSmithKline (CASE award to R.J.P.) for
funding. The EPSRC National Mass Spectrometry Service is
gratefully acknowledged for running mass spectra. The EPSRC
National Crystallography Service51 is gratefully acknowledged
for obtaining and determining all xray structures.
(39) Diez-Poza, C.; Barbero, A. Eur. J. Org. Chem. 2017, 2017, 4651.
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