Enantioselective synthesis of syn- and anti-1,3-diols via allyltitanation of unprotected β-hydroxyaldehydes

Organic Letters

Volumn 2, Issue 4, 2000, Pages 501-504

  BouzBouz, Samir ^a   Cossy, Janine ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000857842     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991349y     Document Type: Article

References (33)

1. (a) Oishi, T.; Nakata, T. Synthesis 1990, 635.
2. (b) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021.
3. (a) Narasaka, K.; Pai, F.-C. Chem. Lett. 1980, 1415.
4. (b) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233.
5. (c) Chen, K. M.; Hardtmann, G. E.; Prasad, K. Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1987, 28 155.
6. (d) Chen, K. M.; Gunderson. K. G.; Hardtmann, G. E.; Prasad, K. Repic, O.; Shapiro, M. J. Chem. Lett. 1987, 1923.
7. (a) Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761.
8. (b) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
9. (c) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447.
10. Rychnovsky, S. D.; Griesgraber G. J. Org. Chem. 1992, 57, 1559.
11. Weigand, S.; Brückner, R. Synlett 1997, 225.
12. Rychnovsky, S. D.; Mickus, D. E. Tetrahedron Lett. 1989, 30, 3011.
13. Rychnovsky, S. D.; Skalitzky, D. J. J. Org. Chem. 1992, 57, 4336.
14. Graner, P.; Anderson, J. T. Org. Lett. 1999, 1, 1057.
15. Ley, S. V.; Anthony, N. J.; Armstrong, A.; Brasca, M. G.; Clarke, T.; Culshaw, D.; Greck, C.; Grice, P.; Jones, A. B.; Lygo, B.; Madin, A.; Sheppard, R. N.; Slawin, A. M. Z.; Williams, D. J. Tetrahedron 1989, 45, 7161.
16. Rychnovsky, S. D.; Griesgraber, G.; Zeller, S.; Skalitzky, D. J. J. Org. Chem. 1991, 56, 5161.
17. Smith, A. B.. III; Pitram, S. M. Org. Lett. 1999, 1, 2001.
18. Lipshutz, B. H.; Moretti, R. Crow, R. Tetrahedron Lett. 1989, 30, 15.
19. Enders, D.; Hendertmark, T. Tetrahedron Lett. 1999, 40, 4169.
20. (a) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 23, 556.
21. (b) Additions with anti-preference but without chelation control: Evans, D. A.; Duffy, J. L.; Dart, M. J. Tetrahedron Lett. 1994, 35, 8537.
22. Kabalka, G. W.; Narayana, C.; Reddy, N. K. Tetrahedron Lett. 1996, 37, 2181.
23. 2: Schreiber, S. L.; Goulet, M. T. J. Am. Chem. Soc. 1987, 109, 8120.
24. (b) Enolate of (2-hydroxy-1,2,2-triphenylethyl)-acetate: Mahler, U.; Devant, R. M.; Braun, M. Chem. Ber: 1988, 121, 2035.
25. (c) 2,5-Dimethylborolane enolate of (1,1-diethylpropylthio)acetate: Duplantier, A. J.; Masamune, S. J. Am. Chem. Soc. 1990, 112, 7079.
26. (d) 2-(α-Chloroallyl)-4,5-dicyclohexyl-1,3-dioxo-2-borolane: Hoffman, R. W.; Stürmer, R. Synlett 1990, 759.
27. (e) Functionalized organozinc reagents: Soai, K.; Hatanaka, T.; Yamashita, T. J. Chem. Soc., Chem. Commun. 1992, 927. Knochel, P.; Brieden, W.; Rozema, M. J.; Eisenberg, C. Tetrahedron Lett. 1993, 34, 5881, and references cited heiren.
28. (e) Functionalized organozinc reagents: Soai, K.; Hatanaka, T.; Yamashita, T. J. Chem. Soc., Chem. Commun. 1992, 927. Knochel, P.; Brieden, W.; Rozema, M. J.; Eisenberg, C. Tetrahedron Lett. 1993, 34, 5881, and references cited heiren.
29. Hafner, A.; Duthaler, R. O.; Marti, R.; Rihs, G.; Rothe-Streit, P.; Schwarzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321.
30. 2 column (hexane/2-propanol).
31. 13C NMR, IR, MS).
32. Demuth, M.; Ritterskamp, P.; Weight, E.; Schaffner, K. J. Am. Chem. Soc. 1986, 108, 4149.
33. Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31. 945.