-
1
-
-
0007235441
-
-
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.
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(1991)
Organic Reactions
, vol.40
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-
De Lucchi, O.1
Miotti, U.2
Modena, G.3
-
2
-
-
0003540874
-
-
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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-
11944251609
-
-
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.
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(1995)
Chem Rev.
, vol.95
, pp. 1717
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Carreño, M.C.1
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4
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37049076087
-
-
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.
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(1995)
J. Chem. Soc. Perkin Trans. 1
, pp. 2405
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-
Kita, Y.1
Shibata, N.2
Kawano, N.3
Tohjo, T.4
Fujimori, C.5
Matsumoto, K.6
Fujita, S.7
-
5
-
-
0028345692
-
-
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.
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(1994)
Tetrahedron: Asymmetry
, vol.5
, pp. 641
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-
Ferreira, J.T.B.1
Marques, J.A.2
Marino, J.P.3
-
6
-
-
0027527467
-
-
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.
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(1993)
Tetrahedron
, vol.49
, pp. 11263
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Craig, D.1
Daniels, K.2
MacKenzie, A.R.3
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7
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0028944554
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-
a) Bravo, P.; Crucianelli, M.; Zanda, M. Tetrahedron Lett. 1995, 36, 3043.
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(1995)
Tetrahedron Lett.
, vol.36
, pp. 3043
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Bravo, P.1
Crucianelli, M.2
Zanda, M.3
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9
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-
0029117977
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-
Arnone, A.; Bravo, P.; Bruché, L.; Crucianelli, M.; Vichi, L.; Zanda, M. Tetrahedron Lett. 1995, 36, 7301.
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(1995)
Tetrahedron Lett.
, vol.36
, pp. 7301
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Arnone, A.1
Bravo, P.2
Bruché, L.3
Crucianelli, M.4
Vichi, L.5
Zanda, M.6
-
10
-
-
0039885790
-
-
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
-
-
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
-
-
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
-
-
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
-
-
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
-
-
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
-
-
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
-
-
note
-
+, 100).
-
-
-
-
18
-
-
0016397937
-
-
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
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19
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-
0016397937
-
-
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
-
-
note
-
Satisfactory elementary analyses have been obtained for both the difluoroaldehydes 2, obtained from (R)-Z-1c and (R)-E-1c.
-
-
-
-
21
-
-
85033753096
-
-
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
-
-
note
-
3C-Ar).
-
-
-
-
23
-
-
0345715621
-
-
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
-
-
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
-
-
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
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-
85033750726
-
-
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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