Highly stereospecific S(N)2-type displacement of sulfinyl by hydroxy group under Pummerer conditions

Tetrahedron Letters

Volumn 37, Issue 33, 1996, Pages 6005-6006

  Bravo, Pierfrancesco ^a   Zanda, Matteo ^a   Zappalà, Carmela ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; AMINO ACID DERIVATIVE; BUTYRIC ACID DERIVATIVE; SULFOXIDE; THREONINE; TRIFLUOROACETIC ACID;

ARTICLE; ENANTIOMER; STEREOSPECIFICITY; SYNTHESIS;

EID: 0030581404     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01260-9     Document Type: Article

References (13)

1. 1. De Lucchi, O.; Miotti, U.; Modena, G. Organic Reactions; Paquette, L. A. Ed.; John Wiley and Sons: New York, 1991, Vol. 40; pp. 157-406. Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
2. 1. De Lucchi, O.; Miotti, U.; Modena, G. Organic Reactions; Paquette, L. A. Ed.; John Wiley and Sons: New York, 1991, Vol. 40; pp. 157-406. Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
3. 2. Bates, K. A.; Winters, R. T.; Picard, J. A. J. Org. Chem. 1992, 57, 3094-3097 and cited references.
4. 3. (a) Arnone, A.; Bravo, P.; Bruché, L.; Crucianelli, M.; Vichi, L.; Zanda, M. Tetrahedron Lett. 1995, 36, 7301-7304.
5. (b) Arnone, A.; Bravo, P.; Capelli, S.; Meille, S. V.; Zanda, M.; Cavicchio, G.; Crucianelli, M. J. Org. Chem. 1996, 61, 3375-3387. N-Cbz γ-difluoro-β-aminosulfoxides have been recently found to undergo the same non-oxidative PR (unpublished results from these laboratories). We are presently investigating the TFAA promoted PR of the corresponding unfluorinated molecules.
6. 4. Bravo, P.; Capelli, S.; Meille, S. V.; Viani, F.; Zanda, M.; Kukhar, V. P.; Soloshonok, V. A. Tetrahedron: Asymmetry 1994, 5, 2009-2018. Bravo, P.; Zanda, M. et al. Gazz. Chim. Ital. 1996, in press. A new and stereoselective entry to γ-fluoro-β-aminosulfoxides will be reported in the near future.
7. 4. Bravo, P.; Capelli, S.; Meille, S. V.; Viani, F.; Zanda, M.; Kukhar, V. P.; Soloshonok, V. A. Tetrahedron: Asymmetry 1994, 5, 2009-2018. Bravo, P.; Zanda, M. et al. Gazz. Chim. Ital. 1996, in press. A new and stereoselective entry to γ-fluoro-β-aminosulfoxides will be reported in the near future.
8. 5. For an overview on the synthesis of trifluoro threonine and allo-threonine derivatives see: Sting, A. R.; Seebach, D. Tetrahedron 1996, 52, 279-290 and references cited therein.
9. 3) - 36.0.
10. 7. Helmchen, G.; Nill, G.; Flockerzi, D.; Schuhle W.; Youssef, M. S. K. Angew. Chem. Int. Ed. Engl. 1979, 18, 62-63. Bravo, P.; Ganazzoli, F.; Resnati, G.; De Munari, S.; Albinati, A. J. Chem. Res. 1988, (S) 216-217, (M) 1701-1739.
11. 7. Helmchen, G.; Nill, G.; Flockerzi, D.; Schuhle W.; Youssef, M. S. K. Angew. Chem. Int. Ed. Engl. 1979, 18, 62-63. Bravo, P.; Ganazzoli, F.; Resnati, G.; De Munari, S.; Albinati, A. J. Chem. Res. 1988, (S) 216-217, (M) 1701-1739.
12. 8. Hornbuckle, S. F.; Livant, P.; Webb, T. R. J. Org. Chem. 1995, 60, 4153-4159 and quoted references.
13. 9. For another stereoselective one-pot displacement of a sulfinyl group see: Casey, M.; Manage, A. C.; Murphy, P. J. Tetrahedron Lett. 1992, 33, 965-968.