Rapid syntheses of difluorinated polyols using a cleavable carbamate

Chemical Communications

Volumn , Issue 21, 1999, Pages 2183-2184

  Balnaves, Andrew S ^a   Palmer, Michael J ^b   Percy, Jonathan M ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALLYL ALCOHOL; CARBAMIC ACID DERIVATIVE; FLUORINE; POLYOL;

ARTICLE; CHEMICAL MODIFICATION; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033533962     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a907174a     Document Type: Article

References (17)

1. J. A. Howarth, W. M. Owton, J. M. Percy and M. H. Rock, Tetrahedron, 1995, 51, 10 289.
2. J. M. Percy, Top. Curr. Chem., 1997, 193, 131. For recent related chemistry of difluorinated enolates and enols, see I. Fleming, R. S. Roberts and S. C. Smith, J. Chem. Soc., Perkin Trans. 1, 1998, 1215; T. Brigaud, P. Doussot and C. Portella, J. Chem. Soc., Chem. Commun., 1994, 2117; T. Brigaud, O. Lefebvre, R. Plantierroyon and C. Portella, Tetrahedron Lett., 1996, 37, 6115; O. Lefebvre, T. Brigaud and C. Portella, Tetrahedron, 1998, 54, 5939; Y. Kodama, H. Yamane, M. Okumura, M. Shiro and T. Taguchi, Tetrahedron, 1995, 51, 12217; K. Uneyama, K. Maeda, T. Kato and T. Katagiri, Tetrahedron Lett., 1998, 39, 3741; O. Lefebvre, T. Brigaud and C. Portella, Tetrahedron, 1999, 55, 7233.
3. J. M. Percy, Top. Curr. Chem., 1997, 193, 131. For recent related chemistry of difluorinated enolates and enols, see I. Fleming, R. S. Roberts and S. C. Smith, J. Chem. Soc., Perkin Trans. 1, 1998, 1215; T. Brigaud, P. Doussot and C. Portella, J. Chem. Soc., Chem. Commun., 1994, 2117; T. Brigaud, O. Lefebvre, R. Plantierroyon and C. Portella, Tetrahedron Lett., 1996, 37, 6115; O. Lefebvre, T. Brigaud and C. Portella, Tetrahedron, 1998, 54, 5939; Y. Kodama, H. Yamane, M. Okumura, M. Shiro and T. Taguchi, Tetrahedron, 1995, 51, 12217; K. Uneyama, K. Maeda, T. Kato and T. Katagiri, Tetrahedron Lett., 1998, 39, 3741; O. Lefebvre, T. Brigaud and C. Portella, Tetrahedron, 1999, 55, 7233.
4. J. M. Percy, Top. Curr. Chem., 1997, 193, 131. For recent related chemistry of difluorinated enolates and enols, see I. Fleming, R. S. Roberts and S. C. Smith, J. Chem. Soc., Perkin Trans. 1, 1998, 1215; T. Brigaud, P. Doussot and C. Portella, J. Chem. Soc., Chem. Commun., 1994, 2117; T. Brigaud, O. Lefebvre, R. Plantierroyon and C. Portella, Tetrahedron Lett., 1996, 37, 6115; O. Lefebvre, T. Brigaud and C. Portella, Tetrahedron, 1998, 54, 5939; Y. Kodama, H. Yamane, M. Okumura, M. Shiro and T. Taguchi, Tetrahedron, 1995, 51, 12217; K. Uneyama, K. Maeda, T. Kato and T. Katagiri, Tetrahedron Lett., 1998, 39, 3741; O. Lefebvre, T. Brigaud and C. Portella, Tetrahedron, 1999, 55, 7233.
5. J. M. Percy, Top. Curr. Chem., 1997, 193, 131. For recent related chemistry of difluorinated enolates and enols, see I. Fleming, R. S. Roberts and S. C. Smith, J. Chem. Soc., Perkin Trans. 1, 1998, 1215; T. Brigaud, P. Doussot and C. Portella, J. Chem. Soc., Chem. Commun., 1994, 2117; T. Brigaud, O. Lefebvre, R. Plantierroyon and C. Portella, Tetrahedron Lett., 1996, 37, 6115; O. Lefebvre, T. Brigaud and C. Portella, Tetrahedron, 1998, 54, 5939; Y. Kodama, H. Yamane, M. Okumura, M. Shiro and T. Taguchi, Tetrahedron, 1995, 51, 12217; K. Uneyama, K. Maeda, T. Kato and T. Katagiri, Tetrahedron Lett., 1998, 39, 3741; O. Lefebvre, T. Brigaud and C. Portella, Tetrahedron, 1999, 55, 7233.
6. J. M. Percy, Top. Curr. Chem., 1997, 193, 131. For recent related chemistry of difluorinated enolates and enols, see I. Fleming, R. S. Roberts and S. C. Smith, J. Chem. Soc., Perkin Trans. 1, 1998, 1215; T. Brigaud, P. Doussot and C. Portella, J. Chem. Soc., Chem. Commun., 1994, 2117; T. Brigaud, O. Lefebvre, R. Plantierroyon and C. Portella, Tetrahedron Lett., 1996, 37, 6115; O. Lefebvre, T. Brigaud and C. Portella, Tetrahedron, 1998, 54, 5939; Y. Kodama, H. Yamane, M. Okumura, M. Shiro and T. Taguchi, Tetrahedron, 1995, 51, 12217; K. Uneyama, K. Maeda, T. Kato and T. Katagiri, Tetrahedron Lett., 1998, 39, 3741; O. Lefebvre, T. Brigaud and C. Portella, Tetrahedron, 1999, 55, 7233.
7. J. M. Percy, Top. Curr. Chem., 1997, 193, 131. For recent related chemistry of difluorinated enolates and enols, see I. Fleming, R. S. Roberts and S. C. Smith, J. Chem. Soc., Perkin Trans. 1, 1998, 1215; T. Brigaud, P. Doussot and C. Portella, J. Chem. Soc., Chem. Commun., 1994, 2117; T. Brigaud, O. Lefebvre, R. Plantierroyon and C. Portella, Tetrahedron Lett., 1996, 37, 6115; O. Lefebvre, T. Brigaud and C. Portella, Tetrahedron, 1998, 54, 5939; Y. Kodama, H. Yamane, M. Okumura, M. Shiro and T. Taguchi, Tetrahedron, 1995, 51, 12217; K. Uneyama, K. Maeda, T. Kato and T. Katagiri, Tetrahedron Lett., 1998, 39, 3741; O. Lefebvre, T. Brigaud and C. Portella, Tetrahedron, 1999, 55, 7233.
8. J. M. Percy, Top. Curr. Chem., 1997, 193, 131. For recent related chemistry of difluorinated enolates and enols, see I. Fleming, R. S. Roberts and S. C. Smith, J. Chem. Soc., Perkin Trans. 1, 1998, 1215; T. Brigaud, P. Doussot and C. Portella, J. Chem. Soc., Chem. Commun., 1994, 2117; T. Brigaud, O. Lefebvre, R. Plantierroyon and C. Portella, Tetrahedron Lett., 1996, 37, 6115; O. Lefebvre, T. Brigaud and C. Portella, Tetrahedron, 1998, 54, 5939; Y. Kodama, H. Yamane, M. Okumura, M. Shiro and T. Taguchi, Tetrahedron, 1995, 51, 12217; K. Uneyama, K. Maeda, T. Kato and T. Katagiri, Tetrahedron Lett., 1998, 39, 3741; O. Lefebvre, T. Brigaud and C. Portella, Tetrahedron, 1999, 55, 7233.
9. J. M. Percy, Top. Curr. Chem., 1997, 193, 131. For recent related chemistry of difluorinated enolates and enols, see I. Fleming, R. S. Roberts and S. C. Smith, J. Chem. Soc., Perkin Trans. 1, 1998, 1215; T. Brigaud, P. Doussot and C. Portella, J. Chem. Soc., Chem. Commun., 1994, 2117; T. Brigaud, O. Lefebvre, R. Plantierroyon and C. Portella, Tetrahedron Lett., 1996, 37, 6115; O. Lefebvre, T. Brigaud and C. Portella, Tetrahedron, 1998, 54, 5939; Y. Kodama, H. Yamane, M. Okumura, M. Shiro and T. Taguchi, Tetrahedron, 1995, 51, 12217; K. Uneyama, K. Maeda, T. Kato and T. Katagiri, Tetrahedron Lett., 1998, 39, 3741; O. Lefebvre, T. Brigaud and C. Portella, Tetrahedron, 1999, 55, 7233.
10. M. Tsukazaki and V. Snieckus, Tetrahedron Lett., 1993, 34, 411.
11. J. Lee, M. Tsukazaki and V. Snieckus, Tetrahedron Lett., 1993, 34, 415.
12. C. Derwing and D. Hoppe, Synthesis, 1996, 149.
13. A. S. Balnaves, T. Gelbrich, M. B. Hursthouse, M. E. Light, M. J. Palmer and J. M. Percy, J. Chem. Soc., Perkin Trans. 1, 1999, 2525.
14. The non-fluorinated system derived from acetaldehyde enolate proceeds from alkoxide to enolate unhindered by the presence of Lewis acids; see S. Sengupta and V. Snieckus, J. Org. Chem., 1990, 55, 5680.
15. L. M. Harwood, A. C. Manage, S. Robin, S. F. G. Hopes, D. J. Watkin and C. E. Williams, Synlett, 1993, 777.
16. M. Kuroboshi and T. Ishihara, Bull. Chem. Soc. Jpn., 1990, 63, 1185.
17. M. Schlosser, T. Jenny and Y. Guggisberg, Synlett, 1990, 704.