N-(diazoacetyl)oxazolidin-2-thiones as sulfur-donor reagents: Asymmetric synthesis of thiiranes from aldehydes

Angewandte Chemie - International Edition

Volumn 51, Issue 43, 2012, Pages 10856-10860

  Cano, Israel ^a   Gõmez Bengoa, Enrique ^a   Landa, Aitor ^a   Maestro, Miguel ^b   Mielgo, Antonia ^a   Olaizola, Iurre ^a   Oiarbide, Mikel ^a   Palomo, Claudio ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

asymmetric synthesis; diazo compounds; sulfur; thiiranes; ylides

Indexed keywords

ASYMMETRIC SYNTHESIS; CYCLOADDITION REACTION; DIAZO COMPOUNDS; FUNCTIONALIZED; OXAZOLIDINES; OXIRANES; STEREOCENTERS; STEREOSELECTIVE MANNER; THIIRANES; YLIDES;

ALDEHYDES; CYCLOADDITION; ORGANIC COMPOUNDS; RHODIUM; RHODIUM COMPOUNDS;

SULFUR;

ALDEHYDE; ETHYLENE SULFIDE; OXAZOLE DERIVATIVE; OXAZOLIDINE; SULFIDE; SULFUR; THIOKETONE;

ARTICLE; CHEMISTRY; CYCLOADDITION; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; CYCLOADDITION REACTION; OXAZOLES; STEREOISOMERISM; SULFIDES; SULFUR; THIONES;

EID: 84867491286     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201204771     Document Type: Article

References (42)

1. Organosulfur Chemistry in Asymmetric Synthesis (Eds.:, T. Toru, C. Bolm,), Wiley-VCH, Weinheim, 2008
2. M. Mellah, A. Voituriez, E. Schulz, Chem. Rev. 2007, 107, 5133-5209.
3. D. J. Procter, J. Chem. Soc. Perkin Trans. 1 2001, 335-354; for asymmetric synthesis of tertiary thiols and thioethers, see
4. J. Clayden, P. MacLellan, Beilstein J. Org. Chem. 2011, 7, 582-595; for metal-catalyzed C-S bond formation, see
5. T. Kondo, T.-a. Mitsudo, Chem. Rev. 2000, 100, 3205-3220
6. W. Adam, R. M. Bargon, Chem. Rev. 2004, 104, 251-261
7. Y. Zhang, J. Wang, Coord. Chem. Rev. 2010, 254, 941-953.
8. D. A. Evans, K. R. Campos, J. S. Tedrow, F. E. Michael, M. R. Gagné, J. Am. Chem. Soc. 2000, 122, 7905-7920
9. D. Enders, A. Schaadt, Synlett 2002, 498-500: organocatalytic
10. M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem. 2005, 117, 804-807
11. Angew. Chem. Int. Ed. 2005, 44, 794-797
12. G. L. Zhao, R. Rios, J. Vesely, L. Eriksson, A. Cordova, Angew. Chem. 2008, 120, 8596-8600
13. Angew. Chem. Int. Ed. 2008, 47, 8468-8472
14. L. Fang, A. Lin, H. Hu, C. Zhu, Chem. Eur. J. 2009, 15, 7039-7043; metal catalyzed
15. M. Jereb, A. Togni, Chem. Eur. J. 2007, 13, 9384-9392.
16. For a review on asymmetric sulfa-Michael additions, see:, D. Enders, K. Lüttgen, A. A. Narine, Synthesis 2007, 959-980.
17. For a general review on thiiranes, see: "Thiiranes and Derivatives", M. Saito, J. Nakayama, in Science of Syntheses, Houben-Weyl Methods of Molecular Transformations, Vol. 39 (Eds.:, D. Bellus, E. N. Jacobsen, S. V. Ley, R. Noyori, M. Regitz, P. J. Reider, E. Schaumann, I. Shinkai, E. J. Thomas, B. M. Trost, N. Kambe,), Thieme, Stuttgart, 2008, pp. 589-658 and Ref. [2d].
18. C. Zhou, C. Fu, S. Ma, Angew. Chem. 2007, 119, 4457-4459
19. Angew. Chem. Int. Ed. 2007, 46, 4379-4381; oxiranes
20. M. Lee, M. M. Bernardo, S. O. Meroueh, S. Brown, R. Fridman, S. Mobashery, Org. Lett. 2005, 7, 4463-4465; β-thiocyanoalcohols
21. E. Łukowska, J. Plenkiewicz, Tetrahedron: Asymmetry 2007, 18, 1202-1209; synthesis of chiral nonracemic thiiranium ions
22. S. E. Denmark, T. Vogler, Chem. Eur. J. 2009, 15, 11737-11745.
23. C. Palomo, M. Oiarbide, F. Dias, A. Ortiz, A. Linden, J. Am. Chem. Soc. 2001, 123, 5602-5603
24. C. Palomo, M. Oiarbide, F. Dias, R. Lõpez, A. Linden, Angew. Chem. 2004, 116, 3369-3372
25. Angew. Chem. Int. Ed. 2004, 43, 3307-3310
26. C. Palomo, M. Oiarbide, R. Lõpez, P. B. González, E. Gõmez-Bengoa, J. M. Saá, A. Linden, J. Am. Chem. Soc. 2006, 128, 15236-15247.
27. M. P. Doyle, M. A. McKervey, T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, Wiley-Interscience, New York, 1998
28. Z. Zhang, J. Wang, Tetrahedron 2008, 64, 6577-6605
29. M. P. Doyle, R. Duffy, M. Ratnikov, L. Zhou, Chem. Rev. 2010, 110, 704-724
30. H. M. L. Davies, J. R. Deton, Chem. Soc. Rev. 2009, 38, 3061-3071; for the generation of thiocarbonyl ylides, see
31. A. Padwa, Chem. Soc. Rev. 2009, 38, 3072-3081.
32. V. K. Aggarwal, M. Crimmin, S. Riches, in Science of Synthesis, Vol. 37 (Ed.:, C. J. Forsyth,), Thieme, Stuttgart, 2008, pp. 321-406; for leading recent examples, see
33. V. K. Aggarwal, J. P. H. Charmant, D. Fuentes, J. N. Harvey, G. Hynd, D. Ohara, W. Picoul, R. L. Robiette, C. Smith, J.-L. Vasse, C. L. Winn, J. Am. Chem. Soc. 2006, 128, 2105-2114 and references therein. For a mechanistic investigation, see
34. D. R. Edwards, P. Montoya-Peleaz, C. M. Crudden, Org. Lett. 2007, 9, 5481-5484.
35. M. P. Doyle, W. Hu, D. J. Timmons, Org. Lett. 2001, 3, 933-935
36. W.-J. Liu, B.-D. Lv, L.-Z. Gong, Angew. Chem. 2009, 121, 6625-6628
37. Angew. Chem. Int. Ed. 2009, 48, 6503-6506.
38. N. Iranpoor, H. Firouzabadi, A. A. Jafari, Synth. Commun. 2003, 33, 2321-2327.
39. K. T. Potts, E. Houghton, U. P. Singh, J. Org. Chem. 1974, 39, 3627-3631
40. A. Padwa, F. R. Kinder, L. Zhi, Synlett 1991, 287-288
41. A. Padwa, A. C. Flick, H. I. Lee, Org. Lett. 2005, 7, 2925-2928.
42. It has been reported that the treatment of a diazothioamide compound related to 1 with rhodium(II) acetate yielded an stable aromatic mesoionic system:, K. T. Potts, P. Murphy, J. Chem. Soc. Chem. Commun. 1984, 1348-1349.