Addition of Crotyltitanocenes to Aldehydes: Influence of Cyclopentadienyl Substituents on the Diastereoselective Formation of Homoallylic Alcohols

Organometallics

Volumn 7, Issue 11, 1988, Pages 2289-2293

  Collins, Scott ^a   Dean, Warren P ^a   Ward, David G ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011504059     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om00101a007     Document Type: Article

References (21)

1. For discussions of this reaction and the role of the metal see: (a) Hoffman, R. W. Angew. Chem., Int. Ed. Engl 1982, 21, 555. b) Yamamoto, Y.; Maruyama, K. Heterocycles 1982, 18, 357, c) Yamamoto, Y.; Yatagai, H.; Ishihara, Y.; Maeda, N.; Maruyama, K. Tetrahedron 1984, 40, 2239. d) Yamamoto, Y.; Saito, Y.; Maruyama, K. J. Organomet. Chem. 1985, 292, 311. (e) Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Organomet. Chem. 1985, 285, 31.
2. (a) Sato, F.; Iijima, S.; Sato, M. Tetrahedron Lett. 1981, 22, 243. b) Sato, F.; Suzuki, Y.; Sato, M. Tetrahedron Lett 1982, 23, 4589. See also: (c) Klei, B.; Teuben, J. H.; De Liefde Meijer, H. J. J. Chem. Soc., Chem. Commun. 1981, 342. (d) Klei, E.; Teuben, J. H.; De Liefde Meijer, H. J.; Kwak, E. J.; Bruins, A. P. J. Organomet. Chem. 1982, 224, 327.
3. (a) Sato, F.; Uchiyama, H.; Iida, K.; Kobayshi, Y.; Sato, M. J. Chem. Soc., Chem. Commun. 1983, 921. (b) Kobayshi, Y.; Umeyama, K.; Sato, F. J. Chem. Soc., Chem. Commun. 1984, 621.
4. Sullivan, N. F.; Little, W. F. J. Organomet. Chem. 1967, 8, 277.
5. (a) Martin, H. A.; Jellinek, F. J. Organomet. Chem. 1967, 8, 115. (b) Martin, H. A.; Jellinek, F. J. Organomet. Chem. 1966, 6, 293.
6. Ward, D. G.; Collins, S., unpublished results.
7. a) Murphy, P. J.; Procter, G.; Russell, A. T. Tetrahedron Lett. 1987, 28, 2037. (b) Evans, D. A.; McGee, L. R. Tetrahedron Lett. 1981, 21, 3975.
8. -1—Andersson, S.; Carter, R. E.; Drakenburg, T. Acta Chem. Scand., Ser. B 1984, B38, 579.
9. (a) Tri-n-butylcrotylstannane, 10 kbar-2.3:1: see ref 1c. (b) Crotylzirconocenes-2.7:1: Yamamoto, Y.; Maruyama, K. Tetrahedron Lett. 1981, 2985. c) Crotylchromium compounds-2.6:1: Buse, C. T.; Heathcock, C. H. Tetrahedron Lett. 1978, 1685.
10. For an extensive review see: Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1984; Vol. 3, Part B, pp 115–118.
11. For earlier work using chiral titanocene reagents or catalysts see: (a) Sato, F.; Iijima, S.; Sato, M. J. Chem. Soc., Chem. Commun. 1981, 180. (b) Reetz, M. T.; Kyung, S.-H.; Westermann, J. Organometallics 1984, 3, 1716. (c) Pacquette, L. A.; McKinney, J. A.; McLaughlin, M. L. Tetrahedron Lett. 1986, 27, 5599.
12. Jeske, G.; Lauke, H.; Mauermann, H.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8091 and references therein.
13. Manzer, L. Inorg. Synth. 1982, 21, 135.
14. (a) Rautenstrauch, V. Helv. Chim. Acta 1974, 57, 496. (b) Halterman, R. L.; Roush, W. R.; Hoong, L. K. J. Org. Chem. 1987, 52, 1152.
15. Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927.
16. (a) Sucrow, W.; Richter, W. Chem. Ber. 1970, 103, 3771. (b) Hiyama, T.; Okude, Y.; Kimura, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1982, 55, 561.
17. Hoffman, R. W., Zeiss, H.-J. J. Org. Chem. 1981, 46, 1309.
18. Meyers, A. I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309.
19. Heathcock, C. H.; Pirrung, M. C.; Sohn, J. E. J. Org. Chem. 1979, 44, 4294.
20. (a) Canceil, J.; Basselier, J. J.; Jacques, J. Bull. Chem. Soc. Fr. 1967, 1024. (b) Canceil, J.; Jacques, J. J. Bull. Chem. Soc. Fr. 1970, 2180.
21. Matsumoto, T.; Hosoda, Y.; Mori, K.; Fukui, K. Bull. Chem. Soc. Jpn. 1972, 45, 3156.