Diastereoselective addition of (η2-Alkyne)Ti(O-i-Pr)2 complexes to 2,3-O-Isopropylideneglyceraldehyde

Tetrahedron Letters

Volumn 38, Issue 26, 1997, Pages 4619-4622

  Yamashita, Koki ^a   Urabe, Hirokazu ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; TITANIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; REACTION ANALYSIS; STEREOISOMERISM;

EID: 0030900073     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00990-8     Document Type: Article

References (32)

1. 2Ti-complex: (a) Shur, V. B.; Burlakov, V. V.; Vol'pin, M. E. J. Organomet. Chem. 1988, 347, 77-83.
2. (b) Hewlett, D. F.; Whitby, R. J. J. Chem. Soc., Chem. Commun. 1990, 1684-1686.
3. 2Ti-complex: (c) Hill, J. E.; Balaich, G.; Fanwick, E.; Rothwell, I. P. Organometallics 1993, 12, 2911-2924.
4. 2Zr-complex: (d) Buchwald, S. L.; Watson, B. T.; Huffman, J. C. J. Am. Chem. Soc. 1987, 109, 2544-2546.
5. (e) Takagi, K.; Rousset, C. J.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 1440-1442.
6. (f) Takahashi, T.; Kageyama, M.; Denisov, V.; Hara, R.; Negishi, E. Tetrahedron Lett. 1993, 34, 687-690.
7. nNb-complex: (g) Hartung, J. B., Jr.; Pedersen, S. F. J. Am. Chem. Soc. 1989, 111, 5468-5469.
8. (h) Kataoka, Y.; Miyai, J.; Tezuka, M.; Takai, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1990, 31, 369-372.
9. (i) Kataoka, Y.; Miyai, J.; Oshima, K.; Takai, K.; Utimoto, K. J. Org. Chem. 1992, 57, 1973-1981.
10. nTa-complex: (j) Strickler, J. R.; Bruck, M. A.; Wexler, P. A.; Wigley, D. E. Organometallics 1990, 9, 266-273.
11. (k) Kataoka, Y.; Miyai, J.; Tezuka, M.; Takai, K.; Utimoto, K. J. Org. Chem. 1992, 57, 6796-6802. See also ref. 1h.
12. (a) Harada, K.; Urabe, H.; Sato, F. Tetrahedron Lett. 1995, 36, 3203-3206.
13. (b) Takayanagi, Y.; Yamashita, K.; Yoshida, Y. Sato, F. J. Chem. Soc., Chem. Commun. 1996, 1725-1726.
14. (c) Yamashita, K.; Sato, F. Tetrahedron Lett. 1996, 37, 7275-7278.
15. Jurczak, J; Pikil, S.; Bauer, T. Tetrahedron 1986, 42, 447-488.
16. For leading reviews on the addition of organometallic reagents to chiral carbonyl compounds, see: Trost, B. M., Ed. Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol. 1 and Vol. 2.
17. Maier, M. E.; Oost, T. J. Organomet. Chem. 1995, 505, 95-107. Maier, M. E.; Haller, B.-U.; Stumpf, R.; Fischer, H. Synlett 1993, 863-865.
18. Maier, M. E.; Oost, T. J. Organomet. Chem. 1995, 505, 95-107. Maier, M. E.; Haller, B.-U.; Stumpf, R.; Fischer, H. Synlett 1993, 863-865.
19. 4 (0.171 g, 0.60 mmol) in ether (3.5 mL) was added i-PrMgCl (1.60 M in ether, 0.72 mL, 1.15 mmol) at -78 °C under argon. The resulting yellow solution was warmed to -50 °C over 1 h, during which period its color turned brown. After stirring at the same temperature for 2 h, (R)-2,3-O-isopropylideneglyceraldehyde (3) (2.28 M in ether, 0.50 mL, 1.15 mmol) was added at -50 °C and the stirring was continued for 2.5 h at -45 °C. Then the reaction mixture was warmed to 0 °C over 30 min and quenched with water (0.5 mL). To the mixture were added NaF (0.5 g) and Celite (0.6 g). After filtration through a short pad of Celite, the filtrate was concentrated to give an oil, which was purified by chromatography on silica gel to give the title compound (124 mg, 72%) as an oil.
20. Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: Berlin, 1983; p 79. Colvin E. W. Silicon Reagents in Organic Synthesis; Academic Press: London, 1988; p 7.
21. Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: Berlin, 1983; p 79. Colvin E. W. Silicon Reagents in Organic Synthesis; Academic Press: London, 1988; p 7.
22. Suzuki, K.; Yuki, Y.; Mukaiyama, T. Chem. Lett. 1981, 1529-1532.
23. For recent reviews on reactions of organotitanium reagents with carbonyl and related compounds, see: Ferreri, C.; Palumbo, G.; Caputo, R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 139. Reetz, M. T. In Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: Chichester, 1994; p 195.
24. For recent reviews on reactions of organotitanium reagents with carbonyl and related compounds, see: Ferreri, C.; Palumbo, G.; Caputo, R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 139. Reetz, M. T. In Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: Chichester, 1994; p 195.
25. Reetz, M. T. Angew. Chem. Int. Ed. Engl. 1984, 23, 556-569.
26. For an example, see: Bhupathy, M.; Cohen, T. Tetrahedron Lett. 1985, 26, 2619-2622.
27. A derivatization of 4d to a functionalized α-alkylidene-γ-butyrolactone 10, which is a model compound towards the synthesis of litsenolide (ref. 13) and obtusilactone (ref. 14), illustrates such an application. (formula presented)
28. Fujita, E.; Nagao, Y. Bioorg. Chem. 1977, 6, 287-309. Cassedy, J. M.; Byrn, S. R.; Stanus, I. K.; Evans, S. M.; McKenzie, A. J. Med. Chem. 1978, 21, 815-819.
29. Fujita, E.; Nagao, Y. Bioorg. Chem. 1977, 6, 287-309. Cassedy, J. M.; Byrn, S. R.; Stanus, I. K.; Evans, S. M.; McKenzie, A. J. Med. Chem. 1978, 21, 815-819.
30. Rollinson, S. W.; Amos, R. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 4114-4125. Depezay, D. C.; Merrer, Y. L. Carbohydr. Res. 1980, 83, 51-62.
31. Rollinson, S. W.; Amos, R. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 4114-4125. Depezay, D. C.; Merrer, Y. L. Carbohydr. Res. 1980, 83, 51-62.
32. Bal, B. S.; Childers, W. E., Jr.; Pinnick, H. W. Tetrahedron 1981, 37, 2091-2096.