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

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

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EID: 0002965387     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5371     Document Type: Article
Times cited : (17)

References (26)
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    • Paquette, L. A. Ed.; John Wiley and Sons: New York
    • 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.
    • (1991) Organic Reactions , vol.40
    • De Lucchi, O.1    Miotti, U.2    Modena, G.3
  • 2
    • 0003540874 scopus 로고
    • CRC Press: Boca Raton, and following pages
    • 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.
    • (1991) Organic Sulfur Chemistry: Structure and Mechanism , pp. 386
    • Oae, S.1
  • 3
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    • 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.
    • (1995) Chem Rev. , vol.95 , pp. 1717
    • Carreño, M.C.1
  • 4
    • 37049076087 scopus 로고
    • and references therein quoted
    • 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.
    • (1995) J. Chem. Soc. Perkin Trans. 1 , pp. 2405
    • Kita, Y.1    Shibata, N.2    Kawano, N.3    Tohjo, T.4    Fujimori, C.5    Matsumoto, K.6    Fujita, S.7
  • 5
    • 0028345692 scopus 로고
    • and references cited therein
    • 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.
    • (1994) Tetrahedron: Asymmetry , vol.5 , pp. 641
    • Ferreira, J.T.B.1    Marques, J.A.2    Marino, J.P.3
  • 6
    • 0027527467 scopus 로고
    • 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.
    • (1993) Tetrahedron , vol.49 , pp. 11263
    • Craig, D.1    Daniels, K.2    MacKenzie, A.R.3
  • 10
    • 0039885790 scopus 로고
    • 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.
    • (1982) Russ. Chem. Rev. , vol.51 , pp. 736
    • Saloutin, V.I.1    Pashkevich, K.I.2    Postovskii, I.Ya.3
  • 11
    • 0037931052 scopus 로고
    • 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.
    • (1988) J. Org. Chem. , vol.53 , pp. 5088
    • Cushman, M.1    Patel, H.2    McKenzie, A.3
  • 12
    • 1542554216 scopus 로고
    • 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.
    • (1952) J. Am. Chem. Soc. , vol.74 , pp. 3902
    • Mc Bee, E.T.1    Burton, T.M.2
  • 13
    • 0010373704 scopus 로고
    • 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.
    • (1982) J Org. Chem. , vol.47 , pp. 2355
    • Kozarich, J.W.1    Chari, R.V.J.2
  • 14
    • 0003045576 scopus 로고
    • 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.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 4593
    • Kozarich, J.W.1    Chari, R.V.J.2    Wu, J.C.3    Lawrence, T.L.4
  • 15
    • 0029034765 scopus 로고
    • 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.
    • (1995) Synthesis , pp. 654
    • Dondoni, A.1    Boscarato, A.2    Formaglio, P.3    Bègué, J.-P.4    Benayoud, F.5
  • 16
    • 0029655340 scopus 로고    scopus 로고
    • and references therein quoted
    • 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.
    • (1996) Tetrahedron , vol.52 , pp. 199
    • Konno, T.1    Yamazaki, T.2    Kitazume, T.3
  • 17
    • 85033760865 scopus 로고    scopus 로고
    • note
    • +, 100).
  • 18
    • 0016397937 scopus 로고
    • 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.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 1960
    • Ogura, K.1    Tsuchihashi, G.2
  • 19
    • 0016397937 scopus 로고
    • 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.
    • (1979) Bull. Chem. Soc. Jpn. , vol.52 , pp. 2013
    • Ogura, K.1    Ito, Y.2    Tsuchihashi, G.3
  • 20
    • 85033734884 scopus 로고    scopus 로고
    • note
    • Satisfactory elementary analyses have been obtained for both the difluoroaldehydes 2, obtained from (R)-Z-1c and (R)-E-1c.
  • 21
    • 85033753096 scopus 로고    scopus 로고
    • note
    • 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
    • 85033740769 scopus 로고    scopus 로고
    • note
    • 3C-Ar).
  • 23
    • 0345715621 scopus 로고
    • 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.
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 2769
    • Stevens, C.L.1    Hanson, H.T.2    Taylor, K.G.3
  • 24
    • 0029033547 scopus 로고
    • 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.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 4059
    • Compain, P.1    Goré, J.2    Vatèle, J.M.3
  • 25
    • 0029053131 scopus 로고
    • 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.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 4063
  • 26
    • 85033750726 scopus 로고    scopus 로고
    • note
    • 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.


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