Stereoselective nucleophilic epoxidation of hydroxy vinyl sulfoxide derivatives

Tetrahedron Letters

Volumn 37, Issue 37, 1996, Pages 6793-6796

  Fernández De La Pradilla, Roberto ^a   Manzano, Pilar ^a   Priego, Julián ^a   Viso, Alma ^b   Martínez Ripoll, Martín ^c   Rodríguez, Ana ^d  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^c INSTITUTO DE QUÍMICA FÍSICA ROCASOLANO   (Spain)

^d UNIVERSITY OF CASTILLA LA MANCHA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; SULFOXIDE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030576973     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)01481-5     Document Type: Article

References (16)

1. 1. Taken in part from the M.S. Theses of P.M. and J.P., Institute de Química Orgánica, CSIC.
2. 2. Tel: 34-(1)-562-2900, ext 210. Fax: 34-(1)-564-4853. E-mail: RIF@CC.CSIC.ES.
3. 3. Fernández de la Pradilla, R.; Castro, S.; Manzano, P.; Priego, J.; Viso, A. J. Org. Chem. 1996, 61, 3586-3587.
4. 4. (a) Jackson, R. F. W.; Standen, S. P.; Clegg, W.; McCamley, A. J. Chem. Soc., Perkin Trans. 1 1995, 141-148.
5. (b) Jackson, R. F. W.; Standen, S. P.; Clegg, W. J. Chem. Soc., Perkin Trans, 1 1995, 149-156.
6. 5. Bailey, P. L.; Clegg, W.; Jackson, R. F. W.; Meth-Cohn, O. J. Chem. Soc., Perkin Trans. 1 1993, 343-350.
7. 6. Briggs, A. D.; Jackson, R. F. W.; Clegg, W.; Elsegood, M. R. J.; Kelly, J.; Brown, P. A. Tetrahedron Lett. 1994, 35, 6945-6948.
8. 7. Hydroxy vinyl sulfoxides 1 and 2 were prepared in two steps from (-)-menthyl sulfmate. See: (a) Marino, J. P.; Viso, A.; Fernández de la Pradilla, R.; Fernández, P. J. Org. Chem. 1991, 56, 1349-1351. Early experiments involving these substrates, including the X-ray diffraction analysis, were carried out on racemic material; the more significant experiments were then reproduced with enantiomerically pure compounds. Racemic γ-silyloxy vinyl sulfoxides 3 and 4 were prepared by straightforward modifications of the procedures of Rayner for diastereo-and enantiopure materials.
9. 1H NMR spectra of crude reaction mixtures are in parentheses.
10. 8. A related substrate bearing a Ph substituent at the β carbon displayed excellent selectivity (1:20). See ref 4a. For a similar observation see ref 7a.
11. -3.
12. 10. As a result of this study, our tentative stereochemical assignments for epoxides derived from simple E-1-hexenyl p-tolyl sulfoxide (ref 3) are being reevaluated.
13. 11. For leading references see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
14. (b) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961-968.
15. 12. For leading references on synthetic applications of these oxiranes, see : (a) Satoh, T.; Horiguchi, K. Tetrahedron Lett. 1995, 36, 8235-8238.
16. (b) Mori, Y.; Yaegashi, K.; Iwase, K.; Yamamori, Y.; Furukawa, H. Tetrahedron Lett. 1996, 37, 2605-2608.