Synthesis of arylzinc thiolates containing perfluoroalkyl chains. Model catalyst precursors for the enantioselective zinc-mediated 1,2-addition of dialkylzincs to aldehydes in fluorous biphase systems

Organic Letters

Volumn 1, Issue 6, 1999, Pages 853-855

  Kleijn, Henk ^a   Rijnberg, Evelien ^a   Jastrzebski, Johann T B H ^a   Van Koten, Gerard ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001504694     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9907320     Document Type: Article

References (13)

1. de Wolf, A. C. A.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 28, 37 and references therein.
2. Hermann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524.
3. Horváth, I. T.; Rábai, J. Science 1994, 266, 72.
4. Rijnberg, E.; Hovestad, N. J.; Kleij, A. W.; Jastrzebski, J. T. B. H.; Boersma, J.; Janssen, M. D.; Spek A. L.; van Koten, G. Organometallics 1997, 16, 2847.
5. Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833. Hof, R. P.; Poelert, M. A.; Peper, N. C. M. W.; Kellogg, R. Tetrahedron: Asymmetry 1994, 5, 31.
6. Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833. Hof, R. P.; Poelert, M. A.; Peper, N. C. M. W.; Kellogg, R. Tetrahedron: Asymmetry 1994, 5, 31.
7. Kleijn, H.; Jastrzebski, J. T. B. H.; Gossage, R. A.; Kooijman, H.; Spek A. L.; van Koten, G. Tetrahedron 1998, 54, 1145.
8. Obtained from Syncom BV, The Netherlands. Vries, T.; Wynberg, H.; van Echten, E.; Koek, J.; ten Hoeve, W.; Kellogg, R. M.; Broxterman, Q. B.; Minnaard, A.; Kaptein, B.; van der Sluis, S.; Hulshof, L.; Kooistra, J. Angew. Chem., Int. Ed. Engl. 1998, 37, 2349.
9. Jones, F. N.; Vaulx, R. L.; Hauser, C. R. J. Org. Chem. 1963, 28, 3461.
10. Knotter, D. M.; van Maanen, H. L.; Grove, D. M.; Spek, A. L.; van Koten, G. Inorg. Chem. 1991, 30, 3309.
11. Analytical data of compounds 3a-5c are available as Supporting Information.
12. 13C NMR.
13. 2Zn in hexanes and 5 mmol of benzaldehyde were added. Again after 16 h the two phases were separated and the product in the hexane layer was analyzed. This procedure was repeated five times; see Table 2.