Enantioselective Pummerer-Type Rearrangement of γ-Fluoro-β-Enaminosulfoxides: Efficient Approach to Chiral Non-Racemic α,α-N,S-Disubstituted Ketals of β-Fluoro-Pyruvaldehydes

Synlett

Volumn 1996, Issue 3, 1996, Pages 249-251

  Bravo, Pierfrancesco ^a   Crucianelli, Marcello ^b   Fronza, Giovanni ^a   Zanda, Matteo ^a  

^a CNR   (Italy)

^b UNIVERSITY OF L'AQUILA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002965387     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5371     Document Type: Article

References (26)

1. a) For a general review on the Pummerer rearrangement see: De Lucchi, O.; Miotti, U.; Modena, G. Organic Reactions; Paquette, L. A. Ed.; John Wiley and Sons: New York, 1991, Vol. 40. For a discussion on the stereochemical aspects of the Pummerer reaction see: Oae, S. Organic Sulfur Chemistry: Structure and Mechanism, CRC Press: Boca Raton, 1991, p. 386 and following pages.
2. a) For a general review on the Pummerer rearrangement see: De Lucchi, O.; Miotti, U.; Modena, G. Organic Reactions; Paquette, L. A. Ed.; John Wiley and Sons: New York, 1991, Vol. 40. For a discussion on the stereochemical aspects of the Pummerer reaction see: Oae, S. Organic Sulfur Chemistry: Structure and Mechanism, CRC Press: Boca Raton, 1991, p. 386 and following pages.
3. b) For applications of the stereoselective Pummerer reaction in the synthesis of biologically active molecules see: Carreño, M. C. Chem Rev. 1995, 95, 1717. For the stereoselective silicon-induced Pummerer reaction of alkyl sulfoxides see: Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Fujimori, C.; Matsumoto, K.; Fujita, S. J. Chem. Soc. Perkin Trans. 1 1995, 2405 and references therein quoted. For the stereoselective additive Pummerer reaction of vinyl sulfoxides see: Ferreira, J. T. B.; Marques, J. A.; Marino, J. P. Tetrahedron: Asymmetry 1994, 5, 641 and references cited therein. See also: Craig, D.; Daniels, K.; MacKenzie, A. R. Tetrahedron 1993, 49, 11263.
4. b) For applications of the stereoselective Pummerer reaction in the synthesis of biologically active molecules see: Carreño, M. C. Chem Rev. 1995, 95, 1717. For the stereoselective silicon-induced Pummerer reaction of alkyl sulfoxides see: Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Fujimori, C.; Matsumoto, K.; Fujita, S. J. Chem. Soc. Perkin Trans. 1 1995, 2405 and references therein quoted. For the stereoselective additive Pummerer reaction of vinyl sulfoxides see: Ferreira, J. T. B.; Marques, J. A.; Marino, J. P. Tetrahedron: Asymmetry 1994, 5, 641 and references cited therein. See also: Craig, D.; Daniels, K.; MacKenzie, A. R. Tetrahedron 1993, 49, 11263.
5. b) For applications of the stereoselective Pummerer reaction in the synthesis of biologically active molecules see: Carreño, M. C. Chem Rev. 1995, 95, 1717. For the stereoselective silicon-induced Pummerer reaction of alkyl sulfoxides see: Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Fujimori, C.; Matsumoto, K.; Fujita, S. J. Chem. Soc. Perkin Trans. 1 1995, 2405 and references therein quoted. For the stereoselective additive Pummerer reaction of vinyl sulfoxides see: Ferreira, J. T. B.; Marques, J. A.; Marino, J. P. Tetrahedron: Asymmetry 1994, 5, 641 and references cited therein. See also: Craig, D.; Daniels, K.; MacKenzie, A. R. Tetrahedron 1993, 49, 11263.
6. b) For applications of the stereoselective Pummerer reaction in the synthesis of biologically active molecules see: Carreño, M. C. Chem Rev. 1995, 95, 1717. For the stereoselective silicon-induced Pummerer reaction of alkyl sulfoxides see: Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Fujimori, C.; Matsumoto, K.; Fujita, S. J. Chem. Soc. Perkin Trans. 1 1995, 2405 and references therein quoted. For the stereoselective additive Pummerer reaction of vinyl sulfoxides see: Ferreira, J. T. B.; Marques, J. A.; Marino, J. P. Tetrahedron: Asymmetry 1994, 5, 641 and references cited therein. See also: Craig, D.; Daniels, K.; MacKenzie, A. R. Tetrahedron 1993, 49, 11263.
7. a) Bravo, P.; Crucianelli, M.; Zanda, M. Tetrahedron Lett. 1995, 36, 3043.
8. b) Bravo, P.; Zanda, M. et al., J. Org. Chem., submitted for publication.
9. Arnone, A.; Bravo, P.; Bruché, L.; Crucianelli, M.; Vichi, L.; Zanda, M. Tetrahedron Lett. 1995, 36, 7301.
10. To our knowledge, little has been reported on the chemistry of fluoropyruvaldehydes (fluoromethylglyoxals). For a review on fluorinated α-dicarbonyl compounds: Saloutin, V. I.; Pashkevich, K. I.; Postovskii, I. Ya. Russ. Chem. Rev. 1982, 51, 736. For the preparation of trifluoropyruvaldehyde see: Cushman, M.; Patel, H.; McKenzie, A. J. Org. Chem. 1988, 53, 5088. Mc Bee, E. T.; Burton, T. M. J. Am. Chem. Soc. 1952, 74, 3902. For monofluoropyruvaldehyde see: Kozarich, J. W.; Chari, R. V. J. J Org. Chem. 1982, 47, 2355. Kozarich, J. W.; Chari, R. V. J.; Wu, J. C.; Lawrence, T. L. J. Am. Chem. Soc. 1981, 103, 4593. For a recent report on the synthesis of racemic β-fluorinated-α-hydroxy-aldehydes see: Dondoni, A.; Boscarato, A.; Formaglio, P.; Bègué, J.-P.; Benayoud, F. Synthesis 1995, 654. For chiral α-trifluoromethylated aldehydes, also in non-racemic form, see: Konno, T.; Yamazaki, T.; Kitazume, T. Tetrahedron 1996, 52, 199 and references therein quoted.
11. To our knowledge, little has been reported on the chemistry of fluoropyruvaldehydes (fluoromethylglyoxals). For a review on fluorinated α-dicarbonyl compounds: Saloutin, V. I.; Pashkevich, K. I.; Postovskii, I. Ya. Russ. Chem. Rev. 1982, 51, 736. For the preparation of trifluoropyruvaldehyde see: Cushman, M.; Patel, H.; McKenzie, A. J. Org. Chem. 1988, 53, 5088. Mc Bee, E. T.; Burton, T. M. J. Am. Chem. Soc. 1952, 74, 3902. For monofluoropyruvaldehyde see: Kozarich, J. W.; Chari, R. V. J. J Org. Chem. 1982, 47, 2355. Kozarich, J. W.; Chari, R. V. J.; Wu, J. C.; Lawrence, T. L. J. Am. Chem. Soc. 1981, 103, 4593. For a recent report on the synthesis of racemic β-fluorinated-α-hydroxy-aldehydes see: Dondoni, A.; Boscarato, A.; Formaglio, P.; Bègué, J.-P.; Benayoud, F. Synthesis 1995, 654. For chiral α-trifluoromethylated aldehydes, also in non-racemic form, see: Konno, T.; Yamazaki, T.; Kitazume, T. Tetrahedron 1996, 52, 199 and references therein quoted.
12. To our knowledge, little has been reported on the chemistry of fluoropyruvaldehydes (fluoromethylglyoxals). For a review on fluorinated α-dicarbonyl compounds: Saloutin, V. I.; Pashkevich, K. I.; Postovskii, I. Ya. Russ. Chem. Rev. 1982, 51, 736. For the preparation of trifluoropyruvaldehyde see: Cushman, M.; Patel, H.; McKenzie, A. J. Org. Chem. 1988, 53, 5088. Mc Bee, E. T.; Burton, T. M. J. Am. Chem. Soc. 1952, 74, 3902. For monofluoropyruvaldehyde see: Kozarich, J. W.; Chari, R. V. J. J Org. Chem. 1982, 47, 2355. Kozarich, J. W.; Chari, R. V. J.; Wu, J. C.; Lawrence, T. L. J. Am. Chem. Soc. 1981, 103, 4593. For a recent report on the synthesis of racemic β-fluorinated-α-hydroxy-aldehydes see: Dondoni, A.; Boscarato, A.; Formaglio, P.; Bègué, J.-P.; Benayoud, F. Synthesis 1995, 654. For chiral α-trifluoromethylated aldehydes, also in non-racemic form, see: Konno, T.; Yamazaki, T.; Kitazume, T. Tetrahedron 1996, 52, 199 and references therein quoted.
13. To our knowledge, little has been reported on the chemistry of fluoropyruvaldehydes (fluoromethylglyoxals). For a review on fluorinated α-dicarbonyl compounds: Saloutin, V. I.; Pashkevich, K. I.; Postovskii, I. Ya. Russ. Chem. Rev. 1982, 51, 736. For the preparation of trifluoropyruvaldehyde see: Cushman, M.; Patel, H.; McKenzie, A. J. Org. Chem. 1988, 53, 5088. Mc Bee, E. T.; Burton, T. M. J. Am. Chem. Soc. 1952, 74, 3902. For monofluoropyruvaldehyde see: Kozarich, J. W.; Chari, R. V. J. J Org. Chem. 1982, 47, 2355. Kozarich, J. W.; Chari, R. V. J.; Wu, J. C.; Lawrence, T. L. J. Am. Chem. Soc. 1981, 103, 4593. For a recent report on the synthesis of racemic β-fluorinated-α-hydroxy-aldehydes see: Dondoni, A.; Boscarato, A.; Formaglio, P.; Bègué, J.-P.; Benayoud, F. Synthesis 1995, 654. For chiral α-trifluoromethylated aldehydes, also in non-racemic form, see: Konno, T.; Yamazaki, T.; Kitazume, T. Tetrahedron 1996, 52, 199 and references therein quoted.
14. To our knowledge, little has been reported on the chemistry of fluoropyruvaldehydes (fluoromethylglyoxals). For a review on fluorinated α-dicarbonyl compounds: Saloutin, V. I.; Pashkevich, K. I.; Postovskii, I. Ya. Russ. Chem. Rev. 1982, 51, 736. For the preparation of trifluoropyruvaldehyde see: Cushman, M.; Patel, H.; McKenzie, A. J. Org. Chem. 1988, 53, 5088. Mc Bee, E. T.; Burton, T. M. J. Am. Chem. Soc. 1952, 74, 3902. For monofluoropyruvaldehyde see: Kozarich, J. W.; Chari, R. V. J. J Org. Chem. 1982, 47, 2355. Kozarich, J. W.; Chari, R. V. J.; Wu, J. C.; Lawrence, T. L. J. Am. Chem. Soc. 1981, 103, 4593. For a recent report on the synthesis of racemic β-fluorinated-α-hydroxy-aldehydes see: Dondoni, A.; Boscarato, A.; Formaglio, P.; Bègué, J.-P.; Benayoud, F. Synthesis 1995, 654. For chiral α-trifluoromethylated aldehydes, also in non-racemic form, see: Konno, T.; Yamazaki, T.; Kitazume, T. Tetrahedron 1996, 52, 199 and references therein quoted.
15. To our knowledge, little has been reported on the chemistry of fluoropyruvaldehydes (fluoromethylglyoxals). For a review on fluorinated α-dicarbonyl compounds: Saloutin, V. I.; Pashkevich, K. I.; Postovskii, I. Ya. Russ. Chem. Rev. 1982, 51, 736. For the preparation of trifluoropyruvaldehyde see: Cushman, M.; Patel, H.; McKenzie, A. J. Org. Chem. 1988, 53, 5088. Mc Bee, E. T.; Burton, T. M. J. Am. Chem. Soc. 1952, 74, 3902. For monofluoropyruvaldehyde see: Kozarich, J. W.; Chari, R. V. J. J Org. Chem. 1982, 47, 2355. Kozarich, J. W.; Chari, R. V. J.; Wu, J. C.; Lawrence, T. L. J. Am. Chem. Soc. 1981, 103, 4593. For a recent report on the synthesis of racemic β-fluorinated-α-hydroxy-aldehydes see: Dondoni, A.; Boscarato, A.; Formaglio, P.; Bègué, J.-P.; Benayoud, F. Synthesis 1995, 654. For chiral α-trifluoromethylated aldehydes, also in non-racemic form, see: Konno, T.; Yamazaki, T.; Kitazume, T. Tetrahedron 1996, 52, 199 and references therein quoted.
16. To our knowledge, little has been reported on the chemistry of fluoropyruvaldehydes (fluoromethylglyoxals). For a review on fluorinated α-dicarbonyl compounds: Saloutin, V. I.; Pashkevich, K. I.; Postovskii, I. Ya. Russ. Chem. Rev. 1982, 51, 736. For the preparation of trifluoropyruvaldehyde see: Cushman, M.; Patel, H.; McKenzie, A. J. Org. Chem. 1988, 53, 5088. Mc Bee, E. T.; Burton, T. M. J. Am. Chem. Soc. 1952, 74, 3902. For monofluoropyruvaldehyde see: Kozarich, J. W.; Chari, R. V. J. J Org. Chem. 1982, 47, 2355. Kozarich, J. W.; Chari, R. V. J.; Wu, J. C.; Lawrence, T. L. J. Am. Chem. Soc. 1981, 103, 4593. For a recent report on the synthesis of racemic β-fluorinated-α-hydroxy-aldehydes see: Dondoni, A.; Boscarato, A.; Formaglio, P.; Bègué, J.-P.; Benayoud, F. Synthesis 1995, 654. For chiral α-trifluoromethylated aldehydes, also in non-racemic form, see: Konno, T.; Yamazaki, T.; Kitazume, T. Tetrahedron 1996, 52, 199 and references therein quoted.
17. +, 100).
18. A similar reaction was observed by Tsuchihashi and co-workers, when racemic α-methylthio-β-enaminosulfoxides were treated with acetic anhydride and pyridine: Ogura, K.; Tsuchihashi, G. J. Am. Chem. Soc. 1974, 96, 1960. See also: Ogura, K.; Ito, Y.; Tsuchihashi, G. Bull. Chem. Soc. Jpn. 1979, 52, 2013.
19. A similar reaction was observed by Tsuchihashi and co-workers, when racemic α-methylthio-β-enaminosulfoxides were treated with acetic anhydride and pyridine: Ogura, K.; Tsuchihashi, G. J. Am. Chem. Soc. 1974, 96, 1960. See also: Ogura, K.; Ito, Y.; Tsuchihashi, G. Bull. Chem. Soc. Jpn. 1979, 52, 2013.
20. Satisfactory elementary analyses have been obtained for both the difluoroaldehydes 2, obtained from (R)-Z-1c and (R)-E-1c.
21. These compounds can be obtained in good yields upon treatment of the corresponding N-Cbz-β-enaminosulfoxides with NaH in DMF and subsequent addition of allyl or benzyl bromide: see ref. 2b.
22. 3C-Ar).
23. 3 hybridised carbon induced by α-fluorosubstitution. For a recent report on an enantioselective rearrangement of cyclic α-hydroxy-imines to the corresponding α-amino-ketones see: Compain, P.; Goré, J.; Vatèle, J. M. Tetrahedron Lett. 1995, 36, 4059. Ibid. 1995, 36, 4063.
24. 3 hybridised carbon induced by α-fluorosubstitution. For a recent report on an enantioselective rearrangement of cyclic α-hydroxy-imines to the corresponding α-amino-ketones see: Compain, P.; Goré, J.; Vatèle, J. M. Tetrahedron Lett. 1995, 36, 4059. Ibid. 1995, 36, 4063.
25. 3 hybridised carbon induced by α-fluorosubstitution. For a recent report on an enantioselective rearrangement of cyclic α-hydroxy-imines to the corresponding α-amino-ketones see: Compain, P.; Goré, J.; Vatèle, J. M. Tetrahedron Lett. 1995, 36, 4059. Ibid. 1995, 36, 4063.
26. A partial racemization of the aldehydes 2 during the work-up or the purification procedures is not unlikely, so their authentic e.e., just after the rearrangement, could be higher than the values reported in Table 1. We are presently investigating this matter.