Computer-assisted design and synthetic applications of chiral enol borinates: Novel, highly enantioselective aldol reagents

Journal of the Brazilian Chemical Society

Volumn 9, Issue 4, 1998, Pages 319-326

  Gennari, Cesare ^a   Ceccarelli, Simona ^a   Piarulli, Umberto ^a   Aboutayab, Karim ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

Chiral boron enolates; Enantioselective aldol reactions; Paclitaxel; Staline

Indexed keywords

EID: 0032345804     PISSN: 01035053     EISSN: None     Source Type: Journal    
DOI: 10.1590/S0103-50531998000400004     Document Type: Review

References (19)

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2. For a review, see: Bernardi, A.; Gennari, C.; Goodman, J.M.; Paterson, I. Tetrahedron:Asymmetry 1995, 6, 2613.
3. It is more convenient to use the same stereodescriptors for the boron enolates derived from different substrates. As sequence-rule-priority changes passing from ketones (OB > alkyl) to esters (OB < O-alkyl) to thioesters (OB < S-alkyl), we define the enolates as Z(OB) or E(OB)-enolates, conventionally attributing to the OB substituent the highest priority.
4. Gennari, C.; Hewkin, C.T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J.M.; Paterson, I. J. Org. Chem. 1992, 57, 5173.
5. Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618.
6. Bernardi, A.; Comotti, A.; Gennari, C.; Hewkin, C.T.; Goodman, J.; Schlapbach, A.; Paterson, I. Tetrahedron 1994, 50, 1227.
7. Gennari, C.; Vulpetti, A.; Moresca, D.; Pain, G. Tetrahedron Lett. 1994, 35, 4623.
8. (a) Gennari, C.; Pain, G.; Moresca, D. J. Org. Chem. 1995, 60, 6248.
9. (b) Gennari, C.; Moresca, D.; Vulpetti, A.; Pain, G. Tetrahedron 1997, 53, 5593.
10. (a) Gennari, C.; Vulpetti, A.; Moresca, D. Tetrahedron Lett. 1994, 35, 4857.
11. (b) Gennari, C.; Vulpetti, A.; Pain, G. Tetrahedron 1997, 53, 5909.
12. Gennari, C.; Pain, G. Tetrahedron Lett. 1996, 37, 3747.
13. Davis, F.A.; Zhou, P. Tetrahedron Lett. 1994, 35, 7525.
14. For a review, see: Nicolaou, K.C.; Dai, W.-M.; Guy, R.K. Angew.Chem., Int.Ed.Engl. 1994, 33, 15.
15. Gennari, C.; Mongelli, N.; Vanotti, E.; Vulpetti, A. British Patent - Application N. 95/12,471.5, Filed June 20, 1995; PCT Int. Appl. EP 96 - 02409, June 4 1996; WO 97 00,870, Jan 9 1997.
16. (a) Gennari, C.; Donghi, M.; Mongelli, N.; Vanotti, E.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1723.
17. (b) Gennari, C.; Carcano, M.; Donghi, M.; Mongelli, N.; Vanotti, E.; Vulpetti, A. J. Org. Chem. 1997, 62, 4746.
18. Bernardi, A.; Gennari, C.; Raimondi, L.; Villa, M. Tetrahedron 1997, 53, 7705.
19. Gennari, C.; Ceccarelli, S.; Piarulli, U.; Aboutayab, K. unpublished results.