Abstract
The relative importance of steric vs. electrostatic effects in the nucleophilic addition to (4R,6S)-4-(tert-butyldimethylsiloxy)-2,2,6-trimethylcyclohexanone (1), a well-known chiral building block, is investigated.
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Rererences
Pfander, H.Key to Carotenoids; Basel: BirkhÄuser, 1987.
Widmer, E.Pure Appl. Chem. 1985,57, 741.
Lamb, N.; Abrams, S. R.Can. J. Chem. 1990,68, 1151.
Pauli, N.; Séquin, U.; Walter, A.Helv. Chim. Acta 1990,73, 578.
See, e.g., Nógrádi, M.Stereoselective Synthesis, Weinheim, VCH, 1995, p. 135.
Keserü, G. M.; Kovári, Z.; Náray-Szabó, G.J. Chem. Soc. Perkin Trans. 2,1996, 2231.
Náray-Szabó, G.; Ferenczy, G.Chem. Rev. 1995,95, 829.
Keserü, G. M.; Náray-Szabó, G. Presented in part at the International RSC Symposium on “Selectivity in Basic and Organic Chemistry,” Jerusalem, August 1995.
Keserü, G. M.; Kajtár-Peredy, M.; Náray-Szabó, G.Tetrahedron Lett. 1994,35, 9255.
All calculations were performed by SPARTAN 3.1 (1994) package, Wavefunctions, Inc., 18401 Von Karman Avenue, Irvine, California 92715.
West, P.; Waack, R.J. Am. Chem. Soc. 1967,89, 4395.
Lamb, N.; Abrams, S. R.Can. J. Chem. 1990,68, 1151.
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Busch, J., Keserü, G.M., Kovári, Z. et al. Steric vs. electrostatic effects in the nucleophilic addition to a hindered cyclohexanone. Struct Chem 8, 257–261 (1997). https://doi.org/10.1007/BF02252969
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DOI: https://doi.org/10.1007/BF02252969