Diastereo and enantioselective synthesis of 1,2-diols promoted by electrophilic selenium reagents

Phosphorus, Sulfur and Silicon and the Related Elements

Volumn 183, Issue 4, 2008, Pages 956-960

  Santi, C ^a   Tiecco, M ^a   Testaferri, L ^a   Tomassini, C ^a   Santoro, S ^a   Bizzoca, G ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

1,2 Diols; Asymmetric synthesis; Catalysis; Selenium

Indexed keywords

EID: 43149118825     PISSN: 10426507     EISSN: 15635325     Source Type: Journal    
DOI: 10.1080/10426500801900881     Document Type: Conference Paper

References (14)

1. (a) M. Tiecco, L. Testaferri, C. Santi, C. Tomassini, F. Marini, L. Bagnoli, and A. Temperini, Chem. Eur. J., 8, 1118 (2002);
2. (b) M. Tiecco, L. Testaferri, C. Santi, C. Tomassini, F. Marini, L. Bagnoli, and A. Temperini, Angew. Chem. Int. Ed., 42, 3131 (2003);
3. (c) M. Tiecco, L. Testaferri, C. Santi, C. Tomassini, S. Santoro, F. Marini, L. Bagnoli, A. Temperini, and F. Costantino Eur. J. Org. Chem. 4867 (2006);
4. (d) M. Tiecco, L. Testaferri, C. Santi, C. Tomassini, R. Bonini, F. Marini, L. Bagnoli, and A. Temperini Org. Lett., 6, 4751 (2004).
5. (a) M. Tiecco, In Electrophilic Selenium, Selenocyclizations, T. Wirth, Ed. (Springer-Verlag, Heidelberg, 2000) p. 7;
6. (b) Organoselenium Chemistry - A Pratical Approach, T. G. Back, Ed. (Oxford, New York, 2000);
7. (c) T. Wirth, Angew. Chem. Int. Ed., 39, 3742 (2000).
8. (a) M. Tiecco, L. Testaferri, M. Tingoli, and F. Marini Synlett, 373 (1994), and references cited therein;
9. (b) M. Tiecco, L. Testaferri, M. Tingoli, L. Bagnoli, and C. Santi, J. Chem. Soc. Chem. Commun., 637 (1993).
10. (a) S. Fukuzawa, K. Takahashi, H. Kato, and H. Yamazaki, J Org. Chem., 62, 7711 (1997);
11. (b) T. Wirth, S.Hauptli, and M. Leuenberger Tetrahedron Asymmetry, 9, 547 (1998).
12. M. Tiecco, L. Testaferri, M. Tingoli, and F. Marini, J Org. Chem., 56, 5207 (1991), and references cited therein.
13. 3 was used as the solvent and TMS as internal standard. GC-MS analyses were carried out with an HP-6890 gas chromatograph (dimethyl silicone column, 12.5 m) equipped with an HP-5973 mass-selective detector. IR spectra were recorded on a JASCO FT/IR-410 spectrophotometer using a multiple reflection horizontal ATR (HATR) accessory. Optical rotations were measured with a JASCO DIP-1000 digital polarimeter.
14. S. Jonsson, H. Adolfsson, and J.-E. Backvall, Org. Lett., 3, 3463 (2001).