Desymmetrization of meso-dialdehydes with optically active cyclopentadienyldialkoxyallyltitanium complexes

Organic Letters

Volumn 2, Issue 22, 2000, Pages 3449-3451

  BouzBouz, Samir ^a   Popkin, Matthew E ^a   Cossy, Janine ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000719768     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0057434     Document Type: Article

References (20)

1. (a) Paterson, I.; Lister, M. A. Tetrahedron Lett. 1988, 29, 585.
2. (b) Paterson, I.; Norcross, R. D.; Ward, R. A.; Romea, P.; Lister, M. A. J. Am. Chem. Soc. 1994, 116, 11287.
3. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
4. Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769.
5. Willis, M. C. J. Chem. Soc., Perkin Trans. 1 1999, 1765.
6. Harada, T.; Matsuda, Y.; Wada, I.; Uchimura, J.; Oku, A. J. Chem. Soc., Chem. Commun. 1990, 21.
7. (a) Kann, N.; Rein, T. J. Org. Chem. 1993, 58, 3802.
8. (b) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P. O.; Rein, T. J. Org. Chem. 1998, 63, 8284.
9. (a) Oppolzer, W.; De Brabander, J.; Walther, E.; Bernardellini, G.; Tetrahedron Lett. 1995, 36, 4413.
10. (b) De Brabander, J.; Oppolzer, W. Tetrahedron 1997, 53, 9169
11. (a) Hafner, A.; Duthaler, R. O.; Marti, R.; Rihs, J.; Rothe-Streit, P.; Schwarzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321.
12. (b) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807.
13. Reetz, M. T. In Organometallics in Synthesis - A Manual; Schlosser, M., Ed.; John Wiley & Sons: New York, 1994; Chapter 3, p 195.
14. TADDOL refers to the ligand trans-2,2-dimethyl-α,α,α′,α′-tetraphenyl-1, 3-dioxolane-4,5-dimethanol.
15. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
16. Chiral GC-MS was performed using a Hewlett-Packard series II 5890 with a custom-made F5-20% dimethylbutylsilane TB50 in SES column.
17. +) 299.2042, found 299.2037.
18. Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370.
19. 16 are 25.2, 23.3, and 100.5 ppm, respectively. Rogers, B.; Rychnowsky, S. D.; Yang, G. J. Org. Chem. 1993, 58, 3511.
20. +), 297 (14), 213 (6), 184 (9), 173 (19), 111(15), 82 (100), 57 (46).