Abstract
A method that employs stoichiometric quantities of a chiral auxiliary for the preparation of highly enantiomerically enriched compounds might in principle appear to be non competitive with an asymmetric catalytic procedure. This would seem particularly true for the synthesis of vicinal diols and α-aminoacids in light of the impressive achievements in the asymmetric dihydroxylation of olefins,1 the resolution of racemic 1,2-diols2 and the hydrogenation of α,β-didehydro α-aminoacids.3 However, an auxiliary based protocol could offer some advantage over existing procedures if the level of stereoinduction is uniformly high, regardless of structural variation both of the substrate and the reagents. Another important feature that can raise the value of an auxiliary based method is the possible exploitation of the same auxiliary for different synthetic applications.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
References
Johnson, R. A.; Sharpless, K. B. in: Catalytic Asymmetric Synthesis; Ojima, I., ed. VCH Publishers: Weinheim, 1993; p 227.
Tokunaga, M; Larrow, J. F.; Kakiucki, F.; Jacobsen, E. N.; Science 1997, 277, 936.
Williams, R.M. Synthesis of Optically Active α-Amino Acids; Pergamon Press: Oxford, 1989; p 230. (b)Takaya, H.; Ohta, T.; Noyori, R. in: Catalytic Asymmetric Synthesis; Ojima, I., ed. VCH Publishers: Weinheim, 1993; p 1.
Colombo, L.; Di Giacomo, M.; Brusotti, G.; Milano, E. Tetrahedron Letters 1995, 36, 2863.
Dondoni, A.; Colombo, L. In Advances in the Use of Synthons in Organic Chemistry, Dondoni, A., ed.; JAI Press, London, 1993, p 1.
Quintard, J.-P.; Elissondo, B.; Mouko-Mpegna, D. J. Organomet. Chem. 1983, 251, 175. (b) Quintard, J.-P.; Elissondo, B.; Jousseaume, B. Synthesis 1984, 495.
Shiner, C. S.; Tsunoda, T.; Goodman, B. A.; Ingham, S.; Lee, S. J. Am. Chem. Soc. 1989, 111, 1381.
Colombo, L.; Di Giacomo, M.; Brusotti, G.; Delogu, G. Tetrahedron Letters 1994, 35, 2063.
Manzoni, L.; Pilati, T.; Poli, G.; Scolastico, C. J. Chem. Soc. Chem. Comm. 1992, 1027. (b) Poli, G.; Maccagni, E.; Manzoni, L.; Pilati, T.; Scolastico, C. Tetrahedron, 1997, 53, 1759.
Frieboes, K. C; Harder, T.; Aulbert, D.; Strahringer, C; Boite, M.; Hoppe, D. Synlett 1993, 921. (b) Harder, T.; Lohl, T.; Boite, M.; Wagner, K.; Hoppe, D. Tetrahedron Letters 1994, 35, 7365.
Kouklovsky, C; Pouilhé, A.; Langlois, Y. J. Am. Chem. Soc. 1990, 112, 6672.
Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155. (b) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277. (c) Ireland, R. E.; Longbin, L. J. Org. Chem. 1993, 58, 2899.
MacroModel V3.5X: Mohamadi, F.; Richards, N. G. J.; Guida, W. C; Liskamp, R.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990,11, 440.
Chérest, M.; Felkin, H. Tetrahedron Letters 1968, 2205. (b) Anh, N. T.; Eisenstein, O. Nouv. J. Chimie 1977, 1, 61.
Ko, K.-Y.; Park, J.-Y. Tetrahedron Letters 1997, 38, 407.
Agami, C; Couty, F.; Mathieu, H. Tetrahedron Letters 1998, 39, 3505.
Heathcock, C. H.; Flippin, L. A. J. Am. Chem. Soc. 1983, 705, 1667. (b) Lodge, E. P.;Heathcock, C. H. J. Am. Chem. Soc. 1987, 109, 2819.
Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem. Int. Ed. Engl. 1985, 24, 1.
Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149. (b) Reetz, M. Angew. Chem. Int. Ed. Engl. 1991, 30, 1531.
Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895.
Lubell, W.; Rapoport, H. J. Org. Chem. 1998, 54, 3824. (b) Muralidharan, K. R.; Mokhallalati M. K.; Pridgen L. N. Tetrahedron Letters 1994, 35, 7489.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1999 Springer Science+Business Media New York
About this chapter
Cite this chapter
Colombo, L., Di Giacomo, M. (1999). Camphor-Derived 2-Stannyl-N-BOC-1,3-Oxazolidine: A New Versatile Chiral Formylanion Equivalent. In: Scolastico, C., Nicotra, F. (eds) Current Trends in Organic Synthesis. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-4801-0_21
Download citation
DOI: https://doi.org/10.1007/978-1-4615-4801-0_21
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4613-7175-5
Online ISBN: 978-1-4615-4801-0
eBook Packages: Springer Book Archive