A stereoselective synthesis of silylated epoxycyclopentanols bearing four contiguous stereogenic centers

Tetrahedron Letters

Volumn 45, Issue 49, 2004, Pages 9123-9126

  Thorimbert, Serge ^a   Taillier, Catherine ^a   Bareyt, Sébastian ^a   Humilière, Delphine ^a   Malacria, Max ^a  

^a Université Pierre et Marie Curie   (France)

Author keywords

Aldolization; Cyclopentanols; Oxidation; Silicon derivatives

Indexed keywords

CYCLOPENTANONE DERIVATIVE; PALLADIUM;

ALDOL REACTION; ALKYLATION; ALLYLATION; ARTICLE; CHEMICAL REACTION; OXIDATION KINETICS; REACTION ANALYSIS; SILYLATION; STEREOCHEMISTRY;

EID: 8644236493     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.10.017     Document Type: Article

References (32)

1. F. Gilloir, and M. Malacria Tetrahedron Lett. 33 1992 3859 3862
2. C. Courillon, R. Le Fol, E. Vandendris, and M. Malacria Tetrahedron Lett. 38 1997 5493 5496
3. F. Marion, S. Calvet, C. Courillon, and M. Malacria Tetrahedron Lett. 43 2002 3369 3371
4. J.K. MacLead, and K.B. Morris Aust. J. Chem. 48 1995 609 624
5. D. Humilière, S. Thorimbert, and M. Malacria Synlett 1998 1255 1257
6. For a recent non stereoselective one-pot hydrolysis of enamine-aldolization see: D.O. Jang, D.D. Kim, D.K. Pyun, and P. Beak Org. Lett. 5 2003 4155 4157
7. O. Sellier, P. Van de Weghe, and J. Eustache Tetrahedron Lett. 40 1999 5859 5860
8. J.K. Gallos, C.C. Dellios, and E.E. Spata Eur. J. Org. Chem. 2001 79 82
9. O.H. Ko, and J.H. Hong Tetrahedron Lett. 43 2002 6399 6402
10. A. Berecibar, C. Grandjean, and A. Siriwardena Chem. Rev. 99 1999 779 844
11. Epoxycyclopentanols have been recently used to prepare anologues of the anti-HBV agent entecavir, see: E. Ruediger, A. Martel, N. Meanwell, C. Solomon, and B. Turmel Tetrahedron Lett. 45 2004 739 742
12. S. Thorimbert, and M. Malacria Tetrahedron Lett. 37 1996 8483 8486
13. C. Commandeur, S. Thorimbert, and M. Malacria J. Org. Chem. 68 2003 5588 5592
14. All new compounds have been fully characterized by NMR, IR and elemental analysis or HRMS
15. E.M. Annet, S.G. Maroldo, S.L. Schilling, and J.A. Harrelson J. Am. Chem. Soc. 106 1984 6759 6767
16. W.P. Griffith, S.L. Ley, G.P. Withcombe, and A.D. Whithe J. Chem. Soc., Chem. Commun. 1987 1625 2627
17. A. Varvoglis Hypervalent Iodine in Organic Synthesis 1997 Academic London
18. D.B. Dess, and J.C. Martin J. Am. Chem. Soc. 113 1991 7277 7287
19. M. Frigerio, and M. Santagostino Tetrahedron Lett. 35 1994 8019 8022
20. T. Wirth Angew. Chem., Int. Ed. 40 2001 2812 2814
21. Caution: DMP and IBX have been reported to be explosive upon impact and heating over 200°C J.B. Plumb, and D.J. Harper Chem. Eng. News 68 1990 3
22. With some batches of DMP, uncontrollable fast production of cyclopentanol and cyclopentanone was observed
23. Full cristallographic data will be reported in due course
24. 6Si: C, 58.03; H, 8.66. Found: C, 57.88; H 8.71
25. 1H NMR spectra
26. J.J. Eisch, and J.T. Trainor J. Org. Chem. 28 1963 2870 2876
27. 3Si: C, 61.39; H, 8.66. Found: C, 61.71; H 9.05
28. For a preparation of allylsilanes from hydroxyacides see: I. Fleming, S. Gil, A.K. Sarkar, and T. Schmidlin J. Chem. Soc., Perkin Trans. 1 1992 3351 3361
29. [3,2,0] bicyclic β-lactones are usually stable at rt. For a recent enantioselective preparation see: G.S. Cortez, S. Ho Oh, and D. Romo Synlett 2001 1731 1736
30. G.V.B. Madhavan, D.P.C. McGee, R.M. Rydzewski, R. Boehme, J.C. Martin, and E.J. Prisbe J. Med. Chem. 31 1988 1798 1804
31. Intramolecular lactonization of tert-butyl esters have been recently described in the arteannuin B chemical transformation: A.K. Bhattacharya, M. Pal, D.C. Jain, B.S. Joshi, R. Roy, U. Rychlewska, and R.P. Sharma Tetrahedron 59 2003 2871 2876
32. IBX has been prepared following the procedure described in: M. Frigerio, M. Santagodtino, and S. Sputore J. Org. Chem. 64 1999 4537 4538