The Library

Asymmetric organocatalysis of the addition of acetone to 2-nitrostyrene using N-diphenylphosphinyl-1,2-diphenylethane-1,2-diamine (PODPEN)

Tools

Morris, David J., 1974-, Partridge, A. Simon, Manville, Charles, Racys, Daurgidas Tomas, Woodward, G. (Gary), Docherty, Gordon and Wills, Martin. (2010) Asymmetric organocatalysis of the addition of acetone to 2-nitrostyrene using N-diphenylphosphinyl-1,2-diphenylethane-1,2-diamine (PODPEN). Tetrahedron Letters, Vol.51 (No.1). pp. 209-212. ISSN 0040-4039

	PDF (Article text) WRAP_Wills_TL_TETL-D-09-02808_corrected_oct_2009.pdf - Requires a PDF viewer such as GSview, Xpdf or Adobe Acrobat Reader Download (174Kb)
	PDF (Publisher's permissions) RE_Institutional_repository_deposit.pdf Restricted to Repository staff only - Requires a PDF viewer such as GSview, Xpdf or Adobe Acrobat Reader Download (281Kb)

Official URL: http://dx.doi.org/10.1016/j.tetlet.2009.10.131

Abstract

The highly enantioselective addition of acetone to 2-nitrostyrene, using N–diphenylphosphinyl-trans-1,2-diphenylethane-1,2-diamine (PODPEN) as catalyst, is described.

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry
Divisions:	Faculty of Science > Chemistry
Library of Congress Subject Headings (LCSH):	Enantioselective catalysis -- Research, Amines -- Research, Acetone -- Research, Heterogeneous catalysis -- Research
Journal or Publication Title:	Tetrahedron Letters
Publisher:	Elsevier
ISSN:	0040-4039
Date:	6 January 2010
Volume:	Vol.51
Number:	No.1
Number of Pages:	4
Page Range:	pp. 209-212
Identification Number:	10.1016/j.tetlet.2009.10.131
Status:	Peer Reviewed
Access rights to Published version:	Restricted or Subscription Access
Funder:	Engineering and Physical Sciences Research Council (EPSRC), Rhodia Consumer Specialities Ltd.
Grant number:	EP/D031168/1 (EPSRC)
References:	1. (a) Xu, L. W.; Lu, Y. Org. Biomol. Chem. 2008, 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. 2. (a) Eder, U.; Sauer, G.; Weichert, R. Angew. Chem. Int. Ed. 1971, 10, 496-497. (b) Lattanzi, A. Chem. Commun. 2009, 1452-1463. 3. Sulzer-Mosse, S.; Alexakis, A. Chem. Commun. 2007, 3123- 3135. (b) Xu, L.-W.; Luo, J.; Lu, Y. Chem. Commun. 2009, 1807-1821. (c) Xu, L.-W.; Lu, Y. Org. Biomol. Chem. 2008, 6, 2047-2053. 4. (a) Tsogeova, S. B.; Wei, S. Chem. Commun. 2006, 1451- 1453. (b) Huang, H.; Jacobsen, E. N. J. Am. Chem. Soc. 2006, 128, 7170-7171. (c) Mei, K.; Jin, M.; Zhang, S.; Li, P.; Liu, W.; Chen, X.; Xue, F.; Duan, W.;Wang, W. Org. Lett. 2009, 11, 2864-2867. 5. Xue, F.; Zhang, S.; Duan, W.; Wang, W. Adv. Synth. Catal. 2008, 350, 2194-2198. 6. (a) Zhang, X.-J.; Liu, S.-P.; Li, X.-M.; Yan, M.; Chan, A. S. C. Chem. Commun. 2009, 833-835. (b) Liu, S.-P.; Zhang, X.- J.; Lao, J.-H.; Yan, M. ARKIVOC, 2009, 2009, 268-280. 7. (a) Wang, J.; Li, H.; Lou, B.; Zu, L.; Gao, H.; Wang, W. Chem. Eur. J. 2006, 12, 4321-4332. (b) Wang, W.; Li, H.; Wang, J. Tetrahedron Lett. 2005, 46, 5077-5079. 8. Ni, B.; Zhang, Q.; Headley, A. D. Tetrahedron: Asymmetry 2007, 18, 1443-1447. 9. Pansare, S. V.; Kirby, R. L. Tetrahedron, 2009, 65, 4557-4561. 10. Vijaikumar, S.; Dhakshinamoorthy, A.; Pitchumani, K. Appl. Catal. A: Gen. 2008, 340, 25-32. 11. Tan, B.; Zhang, X.; Chua, P. J.; Zhong, G. Chem. Commun. 2009, 779-781. 12. Tan, B.; Zeng, X.; Lu, Y.; Chua, P.J.; Zhong, G. Org. Lett. 2009, 11, 1927-1930. 13. Liu, X.-W.; Le, T. N.; Lu, Y.; Xiao, Y.; Ma, J.; Li, X. Org. Biomol. Chem. 2008, 3997-4003. 14. Yu, G.; Ge, Z.-M.; Cheng, T.-M.; Li, R.-T. Chin. J. Chem. 2008, 26, 911-915. 15. (a) Li, P.; Wang, L.; Zhang, Y.; Wang, G. Tetrahedron, 2008, 64, 7633-7638. (b)Tsandi, E.; Kokotos, C. G.; Kousidou, S.; Ragoussis, V.; Kokotos, G. Tetrahedron, 2009, 65, 1444-1449. (c) Ni, B.; Zhang, Q.; Dhungana, K.; Headley, A. D. Org. Lett. 2009, 11, 1037-1040. (d) Wang, C.; Yu, C.; Liu C.; Peng, Y. Tetrahedron Lett. 2009, 50, 2363-2366. (e) Chaun, Y.; Chen G.; Peng, Y. Tetrahedron Lett. 2009, 50, 3054-3058. (f) Xu, D.-Q.; Yue, H.-D.; Luo, S.-P.; Xia, A.-B.; Zhang, S.; Xu, Z.-Y.; Org. Biomol. Chem. 2008, 6, 2054-2057. (g) Laars, M.; Ausmees, K.; Uudsemaa, M.; Tamm, T.; Kanger, T.; Lopp, M. J. Org. Chem. 2009, 74, 3772-3775. 16. (a) García-García, P.; Ladépêche, A.; Halder, R.; List, B. Angew. Chem. Int. Ed. 2008, 47, 4719-4721 (b) Hayashi, Y.; Itoh, T.; Ohkubo, M.; Ishikawa, H. Angew. Chem. Int. Ed. 2008, 47, 4722-4724. 17. Burns, B.; Gamble, M. P.; Simm, A. R. C.; Studley, J. R.; Alcock, N. W.; Wills, M. Tetrahedron: Asymmetry, 1997, 8, 73-78. 18. Denmark, S. E.; Beutner, G. L.; Angew. Chem. Int. Ed. 2008, 47, 1560-1638. 19. Suzuki, T.; Hiroi, K. J. Tohoku Pharmaceutical University, 2001, 48, 95-98. 20. Bernardi, L.; Bonini, B. F.; Capitò, E.; Dessole, G.; Comes-Ffranchini, M.; Fochi, M.; Ricci, A. J. Org. Chem. 2004, 69, 8168-8171. (b) Kohmura, Y.; Mase, T. J. Org. Chem. 2004, 69, 6329-6334. 21. Tan, K. L.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2007, 46, 1315-1317. 22. Ju, Y.-D.; Xu, L.-W.; Li, L.; Lai, G.-Q.; Qiu, H.-Y.; Jiang, J.-X.; Lu, Y. Tetrahedron Lett. 2008, 49, 6773-6777. 23. In a typical preparation, 10 was made by direct reaction of DPEN with Ph2P(O)Cl, 62% yield on a 0.5g scale, ca. 17% 11 was also formed. 24. Watson, D. A.; Chiu, M.; Bergman, R. G. Organometallics, 2006, 25, 4731-4733. 25. (a) Hine, J. Acc. Chem. Res. 1978, 11, 1. (b) Hine, J. J. Org. Chem. 1981, 46, 649. 26. Dahlin, N.; Bøgevig, A.; Adolfsson, H. Adv. Synth. Catal. 2004, 346, 1101-1105. 27. Rishel, M. J.; Amarasinghe, K. K. D.; Dinn, S. R.; Johnson, B. F. J. Org. Chem. 2009, 74, 4001-4004. 28. Fletcher, D. A.; McMeeking, R. F.; Parkin, D. J. Chem. Inf. Comput. Sci. 1996, 36, 746.
URI:	http://wrap.warwick.ac.uk/id/eprint/3308