Enantioselective organocatalyzed α sulfenylation of aldehydes

Angewandte Chemie - International Edition

Volumn 44, Issue 5, 2005, Pages 794-797

  Marigo, Mauro ^a   Wabnitz, Tobias C ^a   Fielenbach, Doris ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

Aldehydes; Asymmetric catalysis; Enantioselectivity; Organocatalysis; Sulfenylation

Indexed keywords

CATALYSTS; PH EFFECTS;

CHIRAL PYRROLIDINE; ENANTIOSELECTIVITIES; ORGANOCATALYSTS;

ALDEHYDES;

ALDEHYDE DERIVATIVE; ISOVALERALDEHYDE;

ARTICLE; CATALYSIS; ENANTIOMER; HALOGENATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 13444267885     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462101     Document Type: Article

References (44)

1. For some recent reviews, see, for example: a) P. I. Dalko, L. Moisan, Angew. Chem. 2001, 113, 3840; Angew. Chem. Int. Ed. 2801, 40, 3726;
2. For some recent reviews, see, for example: a) P. I. Dalko, L. Moisan, Angew. Chem. 2001, 113, 3840; Angew. Chem. Int. Ed. 2001, 40, 3726;
3. b) B. List, Tetrahedron 2002, 58, 5573;
4. c) R. O. Duthaler, Angew. Chem. 2003, 115, 1005; Angew. Chem. Int. Ed. 2003, 42, 975;
5. c) R. O. Duthaler, Angew. Chem. 2003, 115, 1005; Angew. Chem. Int. Ed. 2003, 42, 975;
6. d) P. Merino, T. Tejero, Angew. Chem. 2004, 116, 3055; Angew. Chem. Int. Ed. 2004, 43, 2995;
7. d) P. Merino, T. Tejero, Angew. Chem. 2004, 116, 3055; Angew. Chem. Int. Ed. 2004, 43, 2995;
8. e) B. List, Acc. Chem. Res. 2004, 37, 548;
9. f) W. Notz, F. Tanaka, C. F. Barbas III, Acc. Chem. Res. 2004, 37, 580;
10. g) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248; Angew. Chem. Int. Ed. 2004, 43, 5138.
11. g) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248; Angew. Chem. Int. Ed. 2004, 43, 5138.
12. a) A. Bøgevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, K. A. Jørgensen, Angew. Chem. 2002, 114, 1868; Angew. Chem. Int. Ed. 2002, 41, 1790;
13. a) A. Bøgevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, K. A. Jørgensen, Angew. Chem. 2002, 114, 1868; Angew. Chem. Int. Ed. 2002, 41, 1790;
14. b) B. List, J. Am. Chem. Soc. 2002, 124, 5656;
15. c) H. Vogt, S. Vanderheiden, S. Bräse, Chem. Commun. 2003, 2448;
16. d) N. Kumaragurubaran, K. Juhl, W. Zhuang, A. Bøgevig, K. A. Jørgensen, J. Am. Chem. Soc. 2002, 124, 6254.
17. a) G. Zhong, Angew. Chem. 2003, 115, 4379; Angew. Chem. Int. Ed. 2003, 42, 4247;
18. a) G. Zhong, Angew. Chem. 2003, 115, 4379; Angew. Chem. Int. Ed. 2003, 42, 4247;
19. b) S. P. Brown, M. P. Brochu, C. J. Sinz, D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 10808;
20. c) Y. Hayashi, J. Yamaguchi, K. Hibino, M. Shoji, Tetrahedron Lett. 2003, 44, 8293;
21. d) A. Córdova, M. Enqvist, I. Ibrahem, J. Casas, J. Am. Chem. Soc. 2004, 126, 8914;
22. e) N. Momiyama, H. Torii, S. Saito, H. Yamamoto, Proc. Natl. Acad. Sci. USA 2004, 101, 5374;
23. f) W. Wang, J. Wang, H. Lia, L. Liao, Tetrahedron Lett. 2004, 45, 7235;
24. g) A. Bøgevig, H. Sundéen, A. Córdova, Angew. Chem. 2004, 116, 1129; Angew. Chem. Int. Ed. 2004, 43, 1109;
25. g) A. Bøgevig, H. Sundéen, A. Córdova, Angew. Chem. 2004, 116, 1129; Angew. Chem. Int. Ed. 2004, 43, 1109;
26. h) Y. Hayashi, J. Yamaguchi, T. Sumaiya, M. Shoji, Angew. Chem. 2004, 116, 1132; Angew. Chem. Int. Ed. 2004, 43, 1112;
27. h) Y. Hayashi, J. Yamaguchi, T. Sumaiya, M. Shoji, Angew. Chem. 2004, 116, 1132; Angew. Chem. Int. Ed. 2004, 43, 1112;
28. i) Y. Hayashi, J. Yamaguchi, T. Sumiya, K. Hibino, M. Shoji, J. Org. Chem. 2004, 69, 5966;
29. j) A. Córdova, H. Sundén, A. Bøgevig, M. Johansson, F. Himo, Chem. Eur. J. 2004, 10, 3673.
30. a) M. P. Brochu, S. P. Brown, D. W. C. MacMillan, J. Am. Chem. Soc. 2004, 126, 4108;
31. b) N. Halland, A. Braunton, S. Bachmann, M. Marigo, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 4790;
32. c) M. Marigo, S. Bachmann, N. Halland, A. Braunton, K. A. Jørgensen, Angew. Chem. 2004, 116, 5623; Angew. Chem. Int. Ed. 2004, 43, 5507.
33. c) M. Marigo, S. Bachmann, N. Halland, A. Braunton, K. A. Jørgensen, Angew. Chem. 2004, 116, 5623; Angew. Chem. Int. Ed. 2004, 43, 5507.
34. See, for example: a) J.-H. Youn, R. Herrmann, I. Ugi, Synthesis 1987, 158 ;
35. b) G. Poli, L. Belvisi, L. Manzoni, C. Scolastico, J. Org. Chem. 1993, 58, 3165;
36. c) D. Enders, T. Schäfer, O. Piva, A. Zamponi, Tetrahedron 1994, 50, 3349;
37. d) K. Chibale, S. Warren, Tetrahedron Lett. 1994, 35, 3991;
38. e) D. Enders, T. Schäfer, W. Mies, Tetrahedron 1998, 54, 10239;
39. f) D. A. Evans, K. R. Campos, J. S. Tedrow, F. E. Michael, M. R. Gagné, J. Am. Chem. Soc. 2000, 122, 7905.
40. T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 3rd ed., Wiley, New York, 1999, p. 458.
41. For a study of electrophilic sulfur reagents that contain nitrogen nucleofuges, see: D. N. Harpp, K. Steliou, T. H. Chan, J. Am. Chem. Soc. 1978, 100, 1222.
42. These additives accelerate enamine formation, but they can racemize tertiary α-sulfenylated aldehydes.
43. The optically active a-sulfenylated aldehyde 3a slowly racemized during column chromatography on silica gel.
44. L. N. Owen, M. B. Rahman, J. Chem. Soc. C 1971, 2432.