Towards the Syntheses of α-Trifluoromethylated Oxygenated Heterocycles and Their Precursors

Steven Harthong; Thierry Billard; Bernard R. Langlois

doi:10.1055/s-2005-872076

FEATUREARTICLE

Towards the Syntheses of α-Trifluoromethylated Oxygenated Heterocycles and Their Precursors

Steven Harthong, Thierry Billard*, Bernard R. Langlois
Laboratoire SERCOF (UMR CNRS 5181), Université Claude Bernard-Lyon 1, Bât. Chevreul, 43 Bd du 11 novembre 1918, 69622 Villeurbanne, France
Fax: +33(4)72431323; e-Mail: billard@univ-lyon1.fr;

Abstract

Alle Artikel dieser Rubrik

Abstract

The possibilities of synthesizing various α-trifluoromethylated oxygenated heterocycles, starting from trifluoroacetaldehyde methyl hemiacetal, through classic cyclization reactions, have been demonstrated. In this way, six-membered cyclic compounds, δ-lactones and also macrolactones, bearing a CF₃ group in a position α to the oxygen could be easily obtained through a RCM reaction. Bicyclic compounds could be also synthesized by an intramolecular Pauson-Khand reaction.

Key words

fluorine - metathesis - cyclizations - oxygenated heterocycles - trifluoroacetaldehyde

Volltext

Referenzen

References

1a Schofield H. J. Fluorine Chem. 1999, 100: 7

1b Groß U. Rüdiger S. In Organofluorine Compounds, Houben-Weyl: Methods of Organic Chemistry Vol. E10a: Baasner B. Hagemann H. Tatlow JC. Georg Thieme; Stuttgart: 1999. p.18-26

1c Smart BE. J. Fluorine Chem. 2001, 109: 3

1d Hiyama T. In Organofluorine Compounds: Chemistry and Properties Springer-Verlag; Berlin: 2000.

1e Dunitz JD. ChemBioChem 2004, 5: 614

1f Dolbier WR. J. Fluorine Chem. 2005, 126: 157

2 Biffinger JC. Kim HW. DiMagno SG. ChemBioChem 2004, 5: 622

3 Ito K, Namekawa M, Ishizuka T, and Nayuki S. inventors; Japanese Patent JP 2000226382. ; Chem. Abstr. 2000, 133, 170332

4 Nakai K. Tagaki Y. Ogawa S. Tsuchiya T. Carbohydr. Res. 1999, 320: 8

5a Takagi Y. Nakai K. Tsuchiya T. Takeuchi T. J. Med. Chem. 1996, 39: 1582

5b Bansal RC. Dean B. Hakomori S.-I. Toyokuni T. J. Chem. Soc., Chem. Commun. 1991, 796

5c Nakai K. Takagi Y. Tsuchiya T. Carbohydr. Res. 1999, 316: 47

6 Hanzawa Y. Uda J. Kobayashi Y. Ishido Y. Taguchi T. Shiro M. Chem. Pharm. Bull. 1991, 39: 2459

7a Hayman CM. Larsen DS. Brooker S. Aust. J. Chem. 1998, 51: 545

7b Hayman CM. Hanton LR. Larsen DS. Guthrie JM. Aust. J. Chem. 1999, 52: 921

8 Leveque L. Le Blanc M. Pastor R. Tetrahedron Lett. 1997, 38: 6001

9 Yamazaki T. Mizutani K. Kitazume T. J. Org. Chem. 1995, 60: 6046

10a Yamazaki T. Mizutani K. Kitazume T. Tetrahedron: Asymmetry 1993, 4: 1059

10b Yamazaki T. Mizutani K. Kitazume T. J. Org. Chem. 1993, 58: 4346

11a Arnone A. Bravo P. Frigerio M. Resnati G. Viani F. J. Chem. Res., Synop. 1989, 278

11b Arnone A. Bravo P. Frigerio M. Resnati G. Viani F. J. Chem. Res., Miniprint 1989, 2201

12 Rychnovsky SD. Hu Y. Ellsworth B. Tetrahedron Lett. 1998, 39: 7271

13 Hanzawa Y. Ishizawa S. Ito H. Kobayashi Y. Taguchi T. J. Chem. Soc., Chem. Commun. 1990, 394

14 Seebach D. Renaud P. Helv. Chim. Acta 1985, 68: 2342

15a Gille S. Ferry A. Billard T. Langlois BR. J. Org. Chem. 2003, 68: 8932

15b Ferry A. Billard T. Langlois BR. Synlett 2005, 1027

For reviews on RCM, see:

16a Fürstner A. Angew. Chem. Int. Ed. 2000, 39: 3012

16b Alkene Metathesis in Organic Synthesis Fürstner A. Springer; Berlin: 1998.

For recent reviews of the PKR, see:

17a Frühauf H.-W. Chem. Rev. 1997, 97: 523

17b Geis O. Schmalz H.-G. Angew. Chem. Int. Ed. 1998, 37: 911

17c Brummond KM. Kent JL. Tetrahedron 2000, 56: 3263

17d Fletcher AJ. Christie SDR. J. Chem. Soc., Perkin Trans. 1 2000, 1657

18a Ishikawa N. Koh MG. Kitazume T. Choi SK. J. Fluorine Chem. 1984, 24: 419

18b Kumar DJS. Madhavan S. Ramachandran PV. Brown HC. Tetrahedron: Asymmetry 2000, 11: 4629

18c Ramachandran PV. Padiya KJ. Rauniyar V. Reddy MVR. Brown HC. Tetrahedron Lett. 2004, 45: 1015

18d Asao N. Liu Pi. Maruoka K. Angew. Chem., Int. Ed. Engl. 1997, 36: 2507

19a Kubota T. Iijima M. Tanaka T. Tetrahedron Lett. 1992, 33: 1351

19b Ishihara T. Hayashi H. Yamanaka H. Tetrahedron Lett. 1993, 34: 5777

19c Loh T.-P. Li X.-R. Tetrahedron 1999, 55: 5611

20a Blond G. Billard T. Langlois BR. J. Org. Chem. 2001, 66: 4826

20b Billard T. Langlois BR. J. Org. Chem. 2002, 67: 997

21 Li C.-J. Chan T.-H. Tetrahedron 1999, 55: 11149

22a Katayma H. Nagao M. Ozawa F. Organometallics 2003, 22: 586

22b Chao W. Weinreb SM. Org. Lett. 2003, 5: 2505

23 Such electrostatic repulsion with a CF₃ group leading to a preferential conformation has been observed: Billard T. Langlois BR. Tetrahedron 1999, 55: 8065

24 Mukai C. Kim JS. Hanaoka M. J. Org. Chem. 1999, 64: 6822

25a Jiang B. Xu M. Angew. Chem. Int. Ed. 2004, 43: 2543

25b Ishizaki M. Iwahara K. Niimi Y. Satoh H. Hoshino O. Tetrahedron 2001, 57: 2729