Enantioselective -chlorination of aldehydes with recyclable fluorous (s)-pyrrolidine-thiourea bifunctional organocatalyst

Synlett

Volumn , Issue 3, 2010, Pages 433-436

  Wang, Liang ^a,c   Cai, Chun ^a   Curran, Dennis P ^b   Zhang, Wei ^c  

^a NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b UNIVERSITY OF PITTSBURGH   (United States)

^c UNIVERSITY OF MASSACHUSETTS BOSTON   (United States)

Author keywords

chlorination; chloroaldehyde; Bifunctional organocatalyst; N chlorosuccinimide (NCS), fluorous catalyst, fluorous solid phase extraction (F SPE)

Indexed keywords

ALDEHYDE; CHLORINE; PYRROLIDINE DERIVATIVE; SUCCINIMIDE DERIVATIVE; THIOUREA;

ARTICLE; CATALYST; CHEMICAL REACTION; CHLORINATION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SOLID PHASE EXTRACTION;

EID: 76249085117     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219198     Document Type: Article

References (31)

1. Berkessel A, Groger H, Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis Wiley-VCH Weinheim 2005
2. Dalko P I., Moisan L, Angew. Chem. Int. Ed. 2004 43 5138
3. Houk K N., List B, Acc. Chem. Res. 2004 37 487
4. List B, Chem. Commun. 2006 819
5. Guillena G, Ramn D J., Tetrahedron: Asymmetry 2006 17 1465
6. Youk S H., Oh S H., Rho H S., Lee J E., Lee J W., Song C E., Chem. Commun. 2009 2220
7. Zhang W, Cai C, Chem. Commun. 2008 5686
8. Zu L, Li H, Wang J, Yu X, Wang W, Tetrahedron Lett. 2006 47 5131
9. Zu L, Wang J, Li H, Wang W, Org. Lett. 2006 8 3077
10. Chu Q, Zhang W, Curran D P., Tetrahedron Lett. 2006 47 9287
11. Zu L, Xie H, Li H, Wang J, Wang W, Org. Lett. 2008 10 1211
12. Zhang W, Curran D P., Tetrahedron 2006 62 11837
13. Thomas G, Medicinal Chemistry: An Introduction Wiley New York 2000
14. De Kimpe N, Verh R, The Chemistry of -Haloketones, -Haloaldehydes, and -Haloimines John Wiley and Sons New York 1988
15. Halland N, Braunton A, Bachmann S, Marigo M, Jrgensen K A., J. Am. Chem. Soc. 2004 126 4790
16. Brochu M P., Brown S P., MacMillan D W. C., J. Am. Chem. Soc. 2004 126 4108
17. For early examples of urea- and thiourea-promoted Claisen, Diels-Alder, and ene reactions, see:, Curran D P., Kuo L H., Tetrahedron Lett. 1995 36 6647
18. Kuo L.-H, PhD Thesis University of Pittsburgh USA 1995
19. For selected examples of thiourea-containing bifunctional catalysts, see:, Takada K, Takada S, Nagasawa K, Synlett 2009 1643
20. Wang S X., Chen F E., Adv. Synth. Catal. 2009 351 547
21. Wang C, Zhou Z, Tang C, Org. Lett. 2008 10 1707
22. Peschiulli A, Gunko Y, Connon S J., J. Org. Chem. 2008 73 2454
23. Yamaoka Y, Miyabe H, Yasui Y, Takemoto Y, Synthesis 2007 2571
24. Cao C L., Sun X L., Zhou J L., Tang Y, J. Org. Chem. 2007 72 4073
25. Hamza A, Schubert G, Soos T, Papai I, J. Am. Chem. Soc. 2006 128 13151
26. Herrera R P., Sgarzani V, Bernardi L, Ricci A, Angew. Chem. Int. Ed. 2005 44 6576
27. Bartoli G, Bosco M, Giuliani A, Mecozzi T, Sambri L, Torregiani E, Marcantoni E, J. Org. Chem. 2002 67 9111
28. Soth M J., Nowick J S., J. Org. Chem. 1999 64 276
29. Berkessel A, Seelig B, Synlett 2009 2113
30. Mei Y, Bentley P A., Du J, Tetrahedron Lett. 2009 50 4199
31. Fluorous columns and products were purchased from Fluorous Technologies, Inc. D.P.C. owns an equity interest in this company.