γ-Chiral β-ketosulfones in asymmetric synthesis: a unified synthetic strategy for enantiopure γ-amino and γ-hydroxy vinyl sulfones-Reference-Cited by-同舟云学术

γ-Chiral β-ketosulfones in asymmetric synthesis: a unified synthetic strategy for enantiopure γ-amino and γ-hydroxy vinyl sulfones

Published:1998-07 Issue:13 Volume:9 Page:2311-2316
ISSN:0957-4166
Container-title:Tetrahedron: Asymmetry
language:en
Short-container-title:Tetrahedron: Asymmetry

Author:

Sengupta Saumitra,Sen Sarma Debarati,Mondal Somnath

Publisher

Elsevier BV

Subject

Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Catalysis

Reference11 articles.

1. Reviews: (a) Simpkins, N. S. Sulfones in Organic Synthesis, Pergamon Press, Oxford, 1993; (b) Simpkins, N. S. Tetrahedron 1990, 46, 6951; (c) Isobe, M. In Perspectives in the Organic Chemistry of Sulfur, Zwanenberg, D.; Klunder, A. J. H., Eds., Elsevier, New York, 1987, Vol. 28, p. 209; (d) Fuchs, P. L.; Braish, T. F. Chem. Rev. 1986, 86, 903.

2. (a) Carretero, J. C.; Arrayas, R. G.; de Gracia, I. S. Tetrahedron Lett. 1997, 38, 8537; (b) Alonso, I.; Carretero, J. C.; Garrido, J. L.; Magro, V.; Pedregal, C. J. Org. Chem. 1997, 62, 5682; (c) Adrio, J.; Carretero, J. C.: Arrayas, R. G. Synlett 1996, 640; (d) Carretero, J. C.; Arrayas, R. G. J. Org. Chem. 1995, 60, 6000; (e) Dominguez, E.; Carretero, J. C. Tetrahedron 1994, 50, 7557 and previous references cited therein.

3. (a) Enders, D.; Jandeleit, B.; von Berg, S. Synlett 1997, 421; (b) Jackson, R. F. W.; Turner, D.; Block, M. H. ibid, 1997, 789; (c) Holzapfel, C. W.; van der Merwe, T. L. Tetrahedron Lett. 1996, 37, 2303; (d) Jackson, R. F. W.; Stander, S. P.; Clegg, W. ibid, 1991, 32, 5393; (e) Burkholder, T. P.; Fuchs, P. L. J. Am. Chem. Soc. 1990, 112, 9601.

4. For some recent studies, see (a) Kauppinen, P. M.; Koskinen, A. M. P. Tetrahedron Lett. 1997, 38, 3103; (b) Reetz, M. T.; Strack, T. J.; Mutulis, F.; Goddard, R. ibid, 1996, 37, 9293; (c) Schreiner, E. P.; Gstach, H. Synlett 1996, 1131; (d) Koskinen, A. M. P. Pure Appl. Chem. 1995, 67, 1031; (e) Plummer, J. S.; Emery, L. A.; Stier, M. A.; Suto, M. J. Tetrahedron Lett. 1993, 34, 7529.

5. There is a solitary report on an enantiopure γ-amino vinyl sulfonate that has been used in peptidomimetic studies: Gennari, C.; Salom, B.; Potenza, D.; Williams, A. Angew. Chem. lnt. Ed. Engl. 1994, 33, 2067.

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