Organozinc Reagents for the Nucleophilic C-Glycosylation of Glycals

Synlett

Volumn 1996, Issue 2, 1996, Pages 185-187

  Thorn, Simon N ^a   Gallagher, Timothy ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000596834     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5346     Document Type: Article

References (16)

1. Postema, M.H.D. Tetrahedron 1992, 48, 8545; Postema, M.H.D. In New Directions in Organic Chemistry; Rees, C.W., Ed.; CRC, 1995.
2. Postema, M.H.D. Tetrahedron 1992, 48, 8545; Postema, M.H.D. In New Directions in Organic Chemistry; Rees, C.W., Ed.; CRC, 1995.
3. Ferrier, R.J.; Prasad, N. J. Chem. Soc (C). 1969, 570.
4. Knochel, P.; Singer, R.D. Chem. Rev. 1993, 93, 2117.
5. Orsini, F., Pelizzoni, F. Carbohydr. Res. 1993, 243, 183.
6. (a) Dunkerton, L.V.; Euske, J.M.; Serino, A.J. Carbohydr. Res. 1987, 171, 89. The use of Pd(0) involves a different mechanistic pathway.
7. (b) For other studies involving the reactivity of organozinc reagents towards conventional O-glycosides, see Kozikowski, A.P.; Konoike, T.; Ritter, A. Carbohydr. Res. 1987, 171, 109
8. (a) Stothers, J.B. Carbon-13 NMR Spectroscopy; Academic: New York, 1973, ch. 3; Kalinowski, H.-O.; Berger S.; Braun, S. Carbon-73 NMR Spectroscopy; Wiley: New York, 1988;
9. (a) Stothers, J.B. Carbon-13 NMR Spectroscopy; Academic: New York, 1973, ch. 3; Kalinowski, H.-O.; Berger S.; Braun, S. Carbon-73 NMR Spectroscopy; Wiley: New York, 1988;
10. (b) For recent applications see: reference 4; Moineau, C.; Bolitt, V.; Sinou, D. J. Chem. Soc., Chem. Commun. 1995, 1103; Brakta, M.; Lhoste, P.; D. Sinou, J. Org. Chem. 1989, 54, 1890.
11. (b) For recent applications see: reference 4; Moineau, C.; Bolitt, V.; Sinou, D. J. Chem. Soc., Chem. Commun. 1995, 1103; Brakta, M.; Lhoste, P.; D. Sinou, J. Org. Chem. 1989, 54, 1890.
12. Sabol, J.S.; Cregge, R.J.; Tetrahedron Lett. 1989, 30, 6271.
13. Knochel, P.; Chou, T.-S.; Jubert C.; Rajagopal, D. J. Org. Chem. 1993, 58, 588.
14. Jubert, C.; Knochel, P. J. Org. Chem. 1992, 57, 5431.
15. Knochel, P.; Yeh, M.C.P.; Berk, S.C.; Talbert, J. J. Org Chem. 1988, 53, 2392.
16. 13C NMR) data has been obtained for all new compounds. Yields refer to isolated material and in most cases the isomeric C-glycosides shown in Tables 1 and 2 were separable by chromatography.