Chiral bis-trifluoromethanesulfonylamide as a chiral Brønsted acid catalyst for the asymmetric hetero Diels-Alder reaction with Danishefsky's diene

Tetrahedron Letters

Volumn 46, Issue 37, 2005, Pages 6355-6358

  Tonoi, Takayuki ^a   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALKADIENE; BISTRIFLUOROMETHANESULFONYLAMIDE; GLYOXYLIC ACID; PHENYLGLYOXAL; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; DIELS ALDER REACTION; HYDROGEN BOND;

BETULACEAE;

EID: 23744450008     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.07.043     Document Type: Article

References (41)

1. R. Noyori Asymmetric Catalysis in Organic Synthesis 1994 Wiley-Interscience New York
2. I. Ojima Catalytic Asymmetric Beller, M Synthesis 1993 VCH New York
3. M. Beller, and C. Bolm Transition Metals for Organic Synthesis 1998 WILEY-VCH Weinheim
4. E.N. Jacobsen, A. Pfaltz, and H. Yamamoto Comprehensive Asymmetric Catalysis 1999 Springer Berlin
5. H.B. Kagan Comprehensive Organic Chemistry 1992 Pergamon Oxford, UK
6. For reviews, see: P.I. Dalko, and L. Moisan Angew. Chem., Int. Ed. 40 2001 3726
7. P.I. Dalko, and L. Moisan Angew. Chem. 113 2001 3840
8. B. List Synlett 2001 1675
9. B. List Tetrahedron 58 2002 5573
10. C.F. Barbas, W. Notz, and F. Tanaka Acc. Chem. Res. 37 2004 580
11. P.R. Schreiner Chem. Soc. Rev. 32 2003 289
12. C. Bolm, T. Rantanen, I. Schiffers, and L. Zani Angew. Chem., Int. Ed. 44 2005 1758
13. For recent examples of chiral Brønsted acid catalysts, see: T. Schuster, M. Bauch, G. Durner, and M.W. Gobel Org. Lett. 2 2000 179
14. N.T. MacDougal, and S.E. Schaus J. Am. Chem. Soc. 125 2003 12094
15. D. Uraguchi, and M. Terada J. Am. Chem. Soc. 126 2004 5356
16. T. Akiyama, J. Itoh, K. Yokota, and K. Fuchibe Angew. Chem., Int. Ed. 43 2004 1566
17. B.M. Nugent, R.A. Yoder, and J.N. Johnston J. Am. Chem. Soc. 126 2004 3418
18. G.D. Joly, and E.N. Jacobsen J. Am. Chem. Soc. 126 2004 4102
19. K. Mikami, O. Kotera, Y. Motoyama, and H. Sakaguchi Synlett 1995 975
20. The best result was obtained by adding 11 equiv of water to the lanthanide complex (88%, 66% ee).
21. For triflylamides as Brønsted acids, see: J.B. Hendrickson, D.D. Sternbach, and K.W. Bair Acc. Chem. Res. 10 1977 306
22. I.A. Koppel, R.W. Taft, F. Anvia, S.Z. Zhu, L.Q. Hu, K.S. Sung, D.D. DesMarteau, L.M. Yagupolskii, Y.L. Yagupolskii, N.V. Ignat'ev, N.V. Kondratenko, A.Y. Volkonskii, V.M. Vlasov, R. Notario, and P.C. Maria J. Am. Chem. Soc. 116 1994 3047
23. a = 7.56): R.D. Trepka, J.K. Harrington, and J.W. Belisle J. Org. Chem. 39 1974 1094
24. F.G. Bordwell, J.C. Brauca, D.L. Hughes, and W.N. Olmstead J. Org. Chem. 45 1980 335
25. Excellent chiral Brønsted acids: Y. Huang, A.K. Unni, A.N. Thadani, and V.H. Rawal Nature 424 2003 146
26. A.N. Thadani, V.H. Stankovic, and V.H. Rawal Proc. Natl. Acad. Sci. U.S.A. 101 2004 5846
27. H. Du, D. Zhao, and K. Ding Chem. Eur. J. 10 2004 5964
28. A.K. Unni, N. Takenaka, H. Yamamoto, and V.H. Rawal J. Am. Chem. Soc. 127 2005 1336 They proposed an intramolecular seven-membered hydrogen bonding rather than the less stable medium-membered double hydrogen bonding in their TADDOL and related systems
29. For the solvent effect on the Diels-Alder reaction, see: J.F. Blake, and W.L. Jorgensen J. Am. Chem. Soc. 113 1991 7430
30. Y. Huang, and V.H. Rawal J. Am. Chem. Soc. 124 2002 9662
31. R.B. Moffett, B. Tiffany, D. Brooke, B.D. Aspergren, and R.V. Heinzelman J. Am. Chem. Soc. 79 1957 1687
32. D.L. Vander Jagt, L.B. Han, and C.H. Lehman J. Org. Chem. 37 1972 4100
33. 3 (0.6 ml) at room temperature.
34. M. Reilly, and T. Oh Tetrahedron Lett. 36 1995 217
35. Double hydrogen bonding activation, see: J. Hine, K. Ahn, J.C. Gallucci, and S.-M. Linden J. Am. Chem. Soc. 106 1984 7980
36. J. Hine, S.-M. Linden, and V.M. Kanagasabapathy J. Org. Chem. 50 1985 5096
37. J. Hine, and K. Ahn J. Org. Chem. 52 1987 2083
38. Review: P.M. Pihko Angew. Chem. 43 2004 2062
39. Double Lewis acid complexation, see: V. Sharma, M. Simard, and J.D. Wuest J. Am. Chem. Soc. 114 1992 7931
40. J.D. Wuest Acc. Chem. Res. 32 1999 81
41. T. Ooi, M. Takahashi, M. Yamada, E. Tayama, K. Omoto, and K. Maruoka J. Am. Chem. Soc. 126 2004 1150