First catalytic enantioselective version of a thia hetero-Diels-Alder reaction with dithioesters

Tetrahedron Letters

Volumn 51, Issue 46, 2010, Pages 6014-6017

  Dentel, Hélne ^a   Chataigner, Isabelle ^b   Le Cavelier, Fabien ^a   Gulea, Mihaela ^a  

^a UNIVERSITÉ DE CAEN   (France)

^b UNIVERSITÉ DE ROUEN   (France)

Author keywords

Asymmetric catalysis; Chiral copper(II) complexes; Dithioester; Thia hetero Diels Alder reaction; Thiopyran

Indexed keywords

1,3 BUTADIENE DERIVATIVE; 2,3 DIMETHYLBUTADIENE; CARBONYL DERIVATIVE; COPPER(II) BIS(OXAZOLINE); CYCLOPENTADIENE DERIVATIVE; DIHYDROTHIOPYRAN DERIVATIVE; DITHIOESTER DERIVATIVE; ESTER DERIVATIVE; LEWIS ACID; OXAZOLINE DERIVATIVE; THIOCARBONYL DIENOPHILE; THIOPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DIELS ALDER REACTION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

ALNUS; THIA;

EID: 77958005316     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.09.055     Document Type: Article

References (43)

1. See, as reviews on this topic: S.M. Weinreb, and R.R. Staib Tetrahedron 38 1982 3087 3128
2. H.B. Kagan, and O. Riant Chem. Rev. 92 1992 1007 1019
3. L.F. Tietze, and G. Kettschau Top. Curr. Chem. 189 1997 1 120
4. E.J. Corey Angew. Chem., Int. Ed. 41 2002 1650 1667
5. K.C. Nicolaou, S.A. Snyder, T. Montagnon, and G.E. Vassilikogiannakis Angew. Chem., Int. Ed. 41 2002 1668 1698
6. H. Pellissier Tetrahedron 65 2009 2839 2877
7. T. Saito, K. Takekawa, J. Nishimura, and M. Kawamura J. Chem. Soc., Perkin Trans. 1 1997 2957 2959
8. T. Saito, K. Takekawa, and T. Takahashi Chem. Commun. 1999 1001 1002
9. B. Heuzé, R. Gasparova, M. Heras, and S. Masson Tetrahedron Lett. 41 2000 7327 7331
10. M. Heras, M. Gulea, S. Masson, and C. Philouze Eur. J. Org. Chem. 2004 160 172
11. R. Bastin, H. Albadri, A.-C. Gaumont, and M. Gulea Org. Lett. 8 2006 1033 1036
12. S. Sinnwell, A.J. Inglis, T.P. Davis, M.H. Stenzel, and C. Barner-Kowollik Chem. Commun. 2008 2052 2054
13. A.J. Inglis, S. Sinnwell, T.P. Davis, C. Barner-Kowollik, and M.H. Stenzel Macromolecules 41 2008 4120 4126
14. A.J. Inglis, S. Sinnwell, M.H. Stenzel, and C. Barner-Kowollik Angew. Chem., Int. Ed. 48 2009 2411 2414
15. See for preparation and use as dienophile: W. Thiel, H. Vida, and R. Mayer Z. Chem. 1977 366 367
16. P. Herczegh, R. Zsely, M. Bognar, and L. Szilagyi Heterocycles 28 1989 887 898
17. Dithioester 3 was synthesized by the same procedure as used for 2, starting from 3-(2-chloroacetyl)oxazolidin-2-one and elemental sulfur.
18. 2-bis(oxazoline)-Lewis acid complexes as catalysts, see: G. Desimoni, G. Faita, and K.A. Jørgensen Chem. Rev. 106 2006 3561 3651
19. A.K. Ghosh, P. Mathivanan, and J. Cappiello Tetrahedron: Asymmetry 9 1998 1 45
20. K.A. Jørgensen, M. Johannsen, S. Yao, H. Audrain, and J. Thorhauge Acc. Chem. Res. 32 1999 605 613
21. J.S. Johnson, and D.A. Evans Acc. Chem. Res. 33 2000 325 335
22. G. Zanoni, F. Castronovo, M. Franzini, G. Vidari, and E. Giannini Chem. Soc. Rev. 32 2003 115 129
23. H.A. McManus, and P.J. Guiry Chem. Rev. 104 2004 4151 4202
24. S. Reymond, and J. Cossy Chem. Rev. 108 2008 5359 5406
25. See, as examples: D.A. Evans, D.M. Barnes, J.S. Johnson, T. Lectka, P. von Matt, S.J. Miller, J.A. Murry, R.D. Norcross, E.A. Shaughnessy, and K.R. Campos J. Am. Chem. Soc. 121 1999 7582 7594
26. A. Landa, B. Richter, R.L. Johansen, A. Minkkilä, and K.A. Jørgensen J. Org. Chem. 72 2007 240 245
27. M. Johannsen, and K.A. Jørgensen J. Org. Chem. 60 1995 5757 5762
28. V.K. Aggarwal, E.S. Anderson, D.E. Jones, K.B. Obierey, and R. Giles Chem. Commun. 1998 1985 1986
29. M.M. Endeshaw, A. Bayer, L.K. Hansen, and O.R. Gautun Eur. J. Org. Chem. 2006 5249 5259
30. S. Yao, S. Saaby, R.G. Hazell, and K.A. Jørgensen Chem. Eur. J. 6 2000 2435 2448
31. All computations have made use of the Gaussian 03 program. Full references are given in Supplementary data.
32. For B3LYP references, see: C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785 789
33. A.D. Becke Phys. Rev. A: At. Mol. Opt. Phys. 38 1988 3098 3100
34. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
35. For 6-31G, see: M.M. Frankl, W.J. Pietro, W.J. Hehre, J.S. Binkley, M.S. Gordon, D.J. DeFrees, and J.A. Pople J. Chem. Phys. 77 1982 3654 3665
36. T. Clark, J. Chandrasekhar, G.W. Spitznagel, and P.V.R. Schleyer J. Comput. Chem. 4 1983 294 301
37. M.J. Frisch, J.A. Pople, and J.S. Binkley J. Chem. Phys. 80 1984 3265 3269
38. For theoretical calculations on dithioester derivatives, see: Y. Wang, X.L. Zeng, and S.J. Shen Chin. J. Struct. Chem. 26 2007 767 772
39. For theoretical studies on reactions of transition-metal complexes, see: S. Niu, and M.B. Hall Chem. Rev. 100 2000 353 405
40. C.J. Cramer, and D.G. Truhlar Phys. Chem. Chem. Phys. 11 2009 10757 10816
41. More details for the theoretical calculations are given in Supplementary data.
42. ‡: gas phase Gibbs energy difference between the optimized transition state and the sum of substrates at 298 K (kcal/mol).
43. 3).