Influence of an ortho-sulfinyl group on the configurational stability of α-lithiated aryloxiranes: deuteration of tolylsulfinyl styrene oxides

Tetrahedron

Volumn 65, Issue 1, 2009, Pages 383-388

  Capriati, Vito ^a   Florio, Saverio ^a   Renzo Luisi, ^a   Salomone, Antonio ^a   Tocco, Maria Giovanna ^a   Martín Castro, Ana M ^b   García Ruano, José Luis ^b   Torrente, Esther ^b  

^a UNIVERSITY OF BARI   (Italy)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

Configurational stability; Lithiation; Phenyl sulfinyl styrene oxide

Indexed keywords

AROMATIC COMPOUND; CARBON; EPOXIDE; ETHYLENE OXIDE DERIVATIVE; FUNCTIONAL GROUP; STYRENE DERIVATIVE;

ARTICLE; EPIMERIZATION; LITHIATION; MOLECULAR STABILITY; OPTICAL ROTATION; PRIORITY JOURNAL; PROTON TRANSPORT; RACEMIZATION; STEREOCHEMISTRY;

EID: 56949100794     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.10.021     Document Type: Article

References (30)

1. Capriati V., Florio S., and Luisi R. Synlett (2005) 1359
2. Chemlà F., and Vrancken E. In: Rappoport Z., and Marek I. (Eds). The Chemistry of Organolithium Compounds Vol. 2 (2004), John Wiley and Sons, New York, NY 1165 Chapter 18
3. Capriati V., Florio S., and Luisi R. Chem. Rev. 108 (2008) 1918
4. Capriati V., Florio S., Luisi R., and Salomone A. Org. Lett. 4 (2002) 2445
5. García Ruano J.L., Carreño M.C., Toledo M.A., Aguirre J.M., Aranda M.T., and Fischer J. Angew. Chem., Int. Ed. 39 (2000) 2736
6. García Ruano J.L., Alemán J., and Soriano J.F. Org. Lett. 5 (2003) 677
7. García Ruano J.L., and Alemán J. Org. Lett. 5 (2003) 4513
8. García Ruano J.L., Alemán J., and Cid M.B. Synthesis (2006) 687
9. Arroyo Y., Meana A., Rodríguez J.F., Santos M., Sanz-Tejedor M.A., and García Ruano J.L. J. Org. Chem. 70 (2005) 3914
10. Arroyo Y., Rodríguez J.F., Santos M., Sanz-Tejedor M.A., and García Ruano J.L. J. Org. Chem. 72 (2007) 1035
11. García Ruano J.L., Alemán J., Alonso I., Parra A., Marcos V., and Aguirre J. Chem.-Eur. J. 13 (2007) 6179
12. García Ruano J.L., Aranda M.T., and Aguirre J.M. Tetrahedron 60 (2004) 5383
13. Lai C.-Y., Mak E.Y., Chan Y., Sau Y.-K., Zhang Q.-F., Lo M.F., Willians I.D., and Leung W.-H. Inorg. Chem. 42 (2003) 5863
14. García Ruano J.L., Martín Castro A.M., Tato F., and Cárdenas D.J. Tetrahedron: Asymmetry 16 (2005) 1963
15. Corey E.J., and Chaykovsky M. J. Am. Chem. Soc. 87 (1965) 1353
16. Jin H., Li Z., and Dong X.-W. Org. Biomol. Chem. 2 (2004) 408
17. Schaus S.E., Brandes B.D., Larrow J.F., Tokunaga M., Hansen K.B., Gould A.E., and Jacobsen E.N. J. Am. Chem. Soc. 124 (2002) 1307
18. Keith J.M., Larrow J.F., and Jacobsen E.N. Adv. Synth. Catal. 343 (2001) 5
19. Brandes B.D., and Jacobsen E.N. Tetrahedron: Asymmetry 8 (1997) 3927
20. Tokunaga M., Larrow J.F., Kakiuchi F., and Jacobsen E.N. Science 277 (1997) 936
21. Akgün E., Glinski M.B., Dhawan K.L., and Durst T.J. J. Org. Chem. 46 (1981) 1165
22. As reported (see Ref. 2), for the lithiation of styrene oxide to occur, an organolithium such as s-BuLi was needed whereas LDA did not work.
23. 1]DIPA was prepared as reported:. Newcomb M., and Reeder R. J. Org. Chem. 45 (1980) 1489
24. Fraser R.R., Bresse M., and Mansour T.S. J. Chem. Soc., Chem. Commun. (1983) 620
25. S)-6 resulted to be 96% enantiomerically enriched.
26. Whisler M.C., NacNeil S.L., Snieckus V., and Beak P. Angew. Chem., Int. Ed. 43 (2004) 2206
27. Le Fur N., Mojovic L., Plé N., Turck A., Reboul V., and Metzner P. J. Org. Chem. 71 (2006) 2609
28. E2-like rear-side attack of a lithium cation or a 'conveyer-belt' delivery mechanism may be playing a role, as reported:. Schlosser M. Organoalkali Chemistry. In: Schlosser M. (Ed). Organometallics in Synthesis: A Manual (2004), Wiley & Sons 52
29. All calculations were performed by SPARTAN, Version 07; Wavefunction: Irvine, CA (USA), 2007.
30. Lin M.-Y., Das A., and Liu R.-S. J. Am. Chem. Soc. 128 (2006) 9340