Additions of allylic indium reagents to aldehydes

Chemtracts

Volumn 10, Issue 7, 1997, Pages 481-496

  Marshall, James A ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

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EID: 28944434581     PISSN: 14319268     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (31)

1. Chao, L.-C., Rieke, R.D. J. Org. Chem. 1975, 40, 2253.
2. For a comprehensive review of organoindium compounds, see Sullivan, A.C. in Dictionary of Organometallic Compounds, Vol. 2, Chapman and Hall: London, 1995, pp. 1975-2008.
3. See also Li, C.-J. Chem. Rev. 1993, 93, 2023.
4. Araki, S., Ito, H., Butsugan, Y. J. Org. Chem. 1988, 53, 1833.
5. See also Araki, S., Shimizu, T., Johar, P.S., Jin, S.-J., Butsugan, Y. J. Org. Chem. 1991, 56, 2538.
6. Li, C. J., Chan, T.H. Tetrahedron Lett. 1991, 32, 7017.
7. Beuchet, P., Marrec, M.L., Mosset, P. Tetrahedron Lett. 1992, 33, 5959.
8. See also Basile, T., Bocoum, A., Savoie, D., Umani-Ronchi, A. J. Org. Chem. 1994, 59, 7766.
9. Paquette, L.A., Mitzel, T.M. J. Am. Chem. Soc. 1996, 118, 1931.
10. Paquette, L.A., Stepanian, M., Mallavadhani, U.V., Cutarelli, T.D., Lowinger, T.B., Klenmeyer, H.J. J. Org. Chem. 1996, 61, 7492.
11. Kim, E., Gordon, D.M., Schmid, W., Whitesides, G.M. J. Org. Chem. 1993, 58, 5500.
12. Gao, J., Härter, R., Gordon, D.M., Whitesides, G.M. J. Org. Chem. 1994, 59, 3714.
13. Binder, W.H., Prenner, R.H., Schmid, W. Tetrahedron 1994, 50, 749.
14. Prenner, R.H., Binder, W.H., Schmid W. Liebigs Ann. Chem. 1994, 73.
15. Isaac, M.B., Chan, T.-H. Tetrahedron Lett. 1995, 36, 8957.
16. Marshall, J.A., Hinkle, K.W. J. Org. Chem. 1995, 60, 1920.
17. Marshall, J.A., Hinkle, K.W. J. Org. Chem. 1996, 61, 105.
18. In designating the steriotriad relationships of diastereomers such as 13.2 as "anti, anti" or "syn, anti" we indicate the mode of addition by the first descriptor and the relationship between the newly formed CHOH Stereocenter and the resident α-center of the aldehyde substrate by the second descriptor.
19. Marshall, J.A., Hinkle, K.W. J. Org. Chem. 1996, 61, 4247.
20. Diana, S.-C.H., Sim, K.-Y., Loh, T.-P. Synlett 1996, 263.
21. Paquette, L.A., Mitzell, T.M. J. Org. Chem. 1996, 61, 8799.
22. For earlier studies from the Paquette group on the influence of solvent and the use of β-hydroxy aldehydes in aqueous solvents, see Paquette, L.A., Mitzel, T.M. Tetrahedron Lett. 1995, 36, 6863.
23. Cf. Keck, G.E., Savin, K.A., Cressman, E.N.K., Abbott, D.E. J. Org. Chem. 1994, 59, 7889.
24. Marshall, J.A., Jablonowski, J.A., Welmaker, G.S. J. Org. Chem. 1996, 61, 2904.
25. Maquire, R.J., Mülzer, J., Bats, J.W. J. Org. Chem. 1996, 61, 6936.
26. Gung, B.W., Melnick, J.P., Wolf, M.A., Marshall, J.A., Beaudoin, S. J. Org. Chem. 1994, 59, 5609.
27. Marshall, J. A., Garofalo, A.W. J. Org. Chem. 1996, 61, 8732.
28. Marshall, J.A., Xie, S. Brazilian J. Chem. 1996, 7, 225.
29. Marshall, J.A., Perkins, J.F., Wolf, M.A. J. Org. Chem. 1995, 60, 5556.
30. Marshall, J.A., Perkins, J.A. J. Org. Chem. 1994, 59, 3509.
31. Lu, Z-H., unpublished results.