Formal desymmetrization by a "Mitsunobu trick" - Enantiomerically pure cis-3,4-Dihydroxypyrroline N-oxides for the enantiodivergent synthesis of trihydroxyindolizidines

European Journal of Organic Chemistry

Volumn , Issue 3, 1998, Pages 419-421

  Cicchi, Stefano ^a   Nunes Jr , José ^a   Goti, Andrea ^a   Brandi, Alberto ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Cyclic nitrones; Desymmetrization; Glycosidase inhibitors; Mitsunobu reaction; Polyhydroxyindolizidines

Indexed keywords

EID: 0001586402     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199803)1998:3<419::AID-EJOC419>3.0.CO;2-V     Document Type: Article

References (27)

1. [1a] A. Brandi, S. Cicchi, F. M. Cordero, R. Frignoli, A. Goti, S. Picasso, P. Vogel, J. Org. Chem. 1995, 60, 6806-6812.
2. [1b] A. Goti, F. Cardona, A. Brandi, S. Picasso, P. Vogel, Tetrahedron: Asymmetry 1996, 7, 1659-1674.
3. A. Goti, F. Cardona, A. Brandi, Synlett 1996, 761-763.
4. [1d] R. Giovannini, E. Marcantoni, M. Petrini, J. Org. Chem. 1995, 60, 5706-5707.
5. [1e] S. Cicchi, A. Goti, A. Brandi, J. Org. Chem. 1995, 60, 4743-4748.
6. [2a] A. E. Mc Caig, R. H. Wightman, Tetrahedron Lett. 1993, 34, 3939-3942.
7. [2b] A. Goti, V. Fedi, L. Nannelli, F. De Sarlo, A. Brandi, Synlett 1997, 577-579.
8. [3a] S. Cicchi, I. Höld, A. Brandi, J. Org. Chem. 1993, 58, 5274-5275.
9. [3b] R. Ballini, E. Marcantoni, M. Petrini, J. Org. Chem. 1992. 57, 1316-1318.
10. [3c] A. Brandi, S. Cicchi, A. Goti, M. Koprowski, K. M. Pietrusiewicz, J. Org. Chem. 1994, 59, 1315-1318.
11. [3d] A. Goti, S. Cicchi, V. Fedi, L. Nannelli, A. Brandi, J. Org. Chem. 1997, 62, 3119-3125.
12. Racemic nitrones 3 have been reported;[4a] Ref. [2a]
13. [4b] J. M. J. Tronchet, G. Zosimo-Landolfo, M. Balkadjian, A. Ricca, M. Zsély, F. Barbalat-Rey, D. Cabrini, P. Lichtle, M. Geoffroy, Tetrahedron Lett. 1991, 32, 4129-4132.
14. For a recent review, see: E. Schoffers, A. Golebiowski, C. R. Johnson, Tetrahedron 1996, 52, 3769-3826.
15. A few nonenzymatic methods have also been reported. For a very recent paper on desymmetrization of a meso-diol using a chiral catalyst, see: M. Kinugasa, T. Harada, A. Oku, J. Am. Chem Soc. 1997, 119, 9067-9068.
16. For reviews on the Mitsunobu reaction, see: [7a] O. Mitsunobu, Synthesis 1981, 1.
17. [7b] B. R. Castro, Org. React 1983, 29, 1.
18. [7c] D. L. Hughes, Org. React. 1992, 42. 335.
19. U. Nagel, E. Kinzel, J. Andrade, G. Prescher, Chem. Ber. 1986, 119, 3326.
20. [9a] S.-I. Murahashi, T. Shiota, Tetrahedron Lett. 1987, 28, 2383.
21. [9b] S.-I. Murahashi, H. Mitsui, T. Shiota, T. Tsuda, S. Watanabe, J. Org. Chem 1990, 55, 1736.
22. [10a] E. Marcantoni, M. Petrini, O. Polimanti, Tetrahedron Lett. 1995. 36, 3561.
23. [10b] A. Goti, L. Nannelli, Tetrahedron Lett. 1996, 37, 6025-6028.
24. [10c] A. Goti, M. Romani, Tetrahedron Lett. 1994, 35, 6567-6570.
25. W. W. Zajac, Jr., T. R. Walters, M. G Darcy. J. Org. Chem. 1988, 53, 5856-5860.
26. [12a] J. J. Tufariello, Ace. Chem. Res. 1979, 12, 396.
27. [12b] J. J. Tufariello, J. P. Tette, J. Org. Chem. 1975, 40, 3866