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Synthesis and use of a stable aminal derived from TsDPEN in asymmetric organocatalysis

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Gosiewska, Silvia, Soni, Rina, Clarkson, Guy J. and Wills, Martin. (2010) Synthesis and use of a stable aminal derived from TsDPEN in asymmetric organocatalysis. Tetrahedron Letters, Vol.51 (No.32). pp. 4214-4217. ISSN 0040-4039

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Official URL: http://dx.doi.org/10.1016/j.tetlet.2010.06.017

Abstract

A stable aminal formed stereoselectively from (R,R)-N-tosyl-1,2-diphenyl-1,2-ethylenediamine (TsDPEN) is capable of asymmetric organocatalysis of Diels-Alder and alpha-amination reactions of aldehydes.

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry
Divisions:	Faculty of Science > Chemistry
Library of Congress Subject Headings (LCSH):	Amines, Catalysis, Chemistry, Organic
Journal or Publication Title:	Tetrahedron Letters
Publisher:	Pergamon
ISSN:	0040-4039
Date:	11 August 2010
Volume:	Vol.51
Number:	No.32
Number of Pages:	4
Page Range:	pp. 4214-4217
Identification Number:	10.1016/j.tetlet.2010.06.017
Status:	Peer Reviewed
Publication Status:	Published
Access rights to Published version:	Open Access
Funder:	University of Warwick, Engineering and Physical Sciences Research Council (EPSRC), Advantage West Midlands (AWM), European Regional Development Fund (ERDF), Birmingham Science City
Grant number:	EP/D031168/1 (EPSRC)
References:	1) (a) Xu, L.-W.; Lu, Y. Org. Biomol. Chem. 2008, 6, 2047- 2053. (b) Melchiorre, P.; Marigo, M.; Carlone, A.; Bartoli, G. Angew. Chem. Int. Ed. 2008, 47, 6138-6171. (c) Dondoni, A.; Massi, A. Angew. Chem. Int. Ed. 2008, 47, 4638-4660. (d) Connon, S. J. Chem. Commun. 2008, 2499-2410. (e) Seayad, J.; List, B. Org. Biomol. Chem. 2005, 3, 719-724. (f) Erkkilả, A.; Majander, I.; P. M. Pihko, P. M. Chem. Rev. 2008, 107, 5416-5470. (g) Mukherjee, S.; Yang, J. W.; Hoffmann, S.; B. List, B. Chem. Rev. 2007, 107, 5471-5569. (h) Lattanzi, A. Chem. Commun. 2009, 1452-1463. (i) Xu, L.-W.; Luo, J.; Y. Lu, Y. Chem. Commun. 2009, 1807-1821. (j) MacMillan, D. W. C. Nature, 2008, 455, 304-308. 2) (a) Eder, U.; Sauer, G.; Weichert, R. Angew. Chem. Int. Edn. 1971, 10, 496-497 Chemical Abstract no. 1972:59072. (b) Hajos, Z. G.; Parrish, D. R. German Patent DE 2102623 1971, (c) Hajos, Z. G.; Parrish. D. R. J. Org. Chem. 1974, 39, 1615-1621. 3) (a) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254-6255. (b) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2002, 41, 1790-1793. (c) List, B.; Lerner, R. A.; Barbas III. C. F. J. Am. Chem. Soc. 2000, 122, 2395-2396. 4) (a) Cobb, A. J. A.; Shaw, D. M.; Longbottom, D. A.; Gold, J. B.; Ley, S. V. Org. Biomol.Chem. 2005, 3, 84-96. (b) Cobb, A. J. A.; Longbottom, D. A.; Shaw, D. M.; Ley, S. V. Chem. Commun. 2004, 1808-1809. 5) (a) Hayashi, Y.; Gotoh, H.; Hayashi, T.; Shoji, M. Angew. Chem. Int. Ed. 2005, 44, 4212-4215. (b) Gu, Q.; Wang, X. F.; Wang, L.; Wu, X. Y.; Zhou. Q. L. Tetrahedron: Asymmetry 2006, 17, 1537-1540. 6) (a) Wang, W.; Wang, J.; Li, H. Angew. Chem. Int. Ed. 2005, 44, 1369-1371. (b) H. Yang, H.; Carter, R. G. Org. Lett. 2008, 10, 4629-4652. (c) Mei, K.; Zhang, S.; He, S.; Li, P.; Jin, M.; Xue, F.; Luo, G.; Zhang, H.; Song, L.; Duan, W.; Wang, W. Tetrahedron Lett. 2008, 49, 2681-2684. 7) (a) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243-4244. (b) Kristensen, T. E.; Vestli, K.; Hansen, F. K.; Hansen, T. Eur. J. Org. Chem. 2009, 30, 5185-5191. (c) Barykina, O. V.; Rossi, K. L.; Rybak, M. J.; Snider, B. B. Org. Lett. 2009, 11, 5334-5337. (d) Brochu, M. P.; Brown, S. P.; MacMillan, D. W C. J. Am. Chem. Soc. 2004, 126, 4108-4109. (e) Peelen, T. J.; Chi, Y.; Gellman, S. H. J. Am. Chem. Soc. 2005, 127, 11598-11599. 8) (a) Mangion, I. K.; Northrup, A, B.; MacMillan, D. W. C.; Angew. Chem. Int. Ed. 2004, 43, 6722-6724. (b) Contad, J. C.; Kog, J.; Laforteza, B. N.;Macmillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 11640-11641. (c) Adolffsson, H. Angew. Chem. Int. Ed. 2005, 44, 3340-3342. (d) Nagib, D. A.; Scott, M. E.; Macmillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 10875-10877. (e) Nicewicz, D. A.; Macmillan, D. W. C. Science 2008, 322, 77-80. 9) (a) Kotrusz, P.; Alemayehu, S.; Toma, S.; Schmalz, H.-G.; Adler, A. Eur. J. Org. Chem. 2005, 4904-4911. (b) Halland, N.; Hansen. T.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, 4955-4957. 10) Bertelsen, S.; Halland, N.; Bachmann, S.; Marigo, M.; Braunton, A.; Jørgensen, K. A. Chem. Commun. 2005, 4821- 4823. 11) Martins, J. E. D.; Clarkson, G. J.; Wills, M. Org. Lett. 2009, 11, 847-850. 12) Cervinka, O.; Kriz, O. Collect. Czech. Chem. Commun. 1968, 33, 2342-2345. 13) Franzen, J.; Marigo, M.; Fielenbch, D.; Wabnitz, T. C.; Kjaersgaard, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 18296-18304. 14) Fletcher, D. A.; McMeeking, R. F.; Parkin,D. J. Chem. Inf. Comput. Sci. 1996, 36, 746-749.
URI:	http://wrap.warwick.ac.uk/id/eprint/5442