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2
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0004252595
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Grieco P.A. (Ed), Blackie Academic & Professional, London
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In: Grieco P.A. (Ed). Organic Synthesis in Water (1998), Blackie Academic & Professional, London
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(1998)
Organic Synthesis in Water
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6
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33845728625
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For a very interesting discussion of enantioselective organocatalysis "in water" or "in the presence of water", see:
-
For a very interesting discussion of enantioselective organocatalysis "in water" or "in the presence of water", see:. Brogan A.P., Dickerson T.J., and Janda K.D. Angew. Chem., Int. Ed. 45 (2006) 8100
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(2006)
Angew. Chem., Int. Ed.
, vol.45
, pp. 8100
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Brogan, A.P.1
Dickerson, T.J.2
Janda, K.D.3
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8
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34147103331
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For a recent contribution from our group, see:
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For a recent contribution from our group, see:. Guizzetti S., Benaglia M., Raimondi L., and Celentano G. Org. Lett. 9 (2007) 1247
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(2007)
Org. Lett.
, vol.9
, pp. 1247
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Guizzetti, S.1
Benaglia, M.2
Raimondi, L.3
Celentano, G.4
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10
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0030038998
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For the synthesis of these silylketene 2-pyridylthioacetals and their use in a non-catalytic synthesis of β-lactams, see:
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For the synthesis of these silylketene 2-pyridylthioacetals and their use in a non-catalytic synthesis of β-lactams, see:. Annunziata R., Cinquini M., Cozzi F., Molteni V., and Schupp O. Tetrahedron 52 (1996) 2573
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(1996)
Tetrahedron
, vol.52
, pp. 2573
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Annunziata, R.1
Cinquini, M.2
Cozzi, F.3
Molteni, V.4
Schupp, O.5
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11
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0345230256
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Annunziata R., Cinquini M., Cozzi F., Molteni V., and Schupp O. J. Org. Chem. 61 (1996) 8293
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(1996)
J. Org. Chem.
, vol.61
, pp. 8293
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Annunziata, R.1
Cinquini, M.2
Cozzi, F.3
Molteni, V.4
Schupp, O.5
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12
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36248939225
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The one-pot formation of the azetidinone ring takes advantage of the excellent leaving group nature of the 2-pyridylthio residue.
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13
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85064667331
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Reviews: and references cited therein
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Reviews:. Kobayashi S. Synlett (1994) 689 and references cited therein
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(1994)
Synlett
, pp. 689
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Kobayashi, S.1
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14
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0000862669
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and references cited therein
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Kobayashi S., and Ishitani H. Chem. Rev. 99 (1999) 1069 and references cited therein
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(1999)
Chem. Rev.
, vol.99
, pp. 1069
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Kobayashi, S.1
Ishitani, H.2
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15
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36248932660
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note
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cis = ca. 5.0-6.0 Hz).
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16
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36248934748
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For a solvent-free, one-pot synthesis of β-lactams, see:
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For a solvent-free, one-pot synthesis of β-lactams, see:. Puglisi A., Benaglia M., and Cozzi F. Eur. J. Org. Chem. (2007) 2865
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(2007)
Eur. J. Org. Chem.
, pp. 2865
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Puglisi, A.1
Benaglia, M.2
Cozzi, F.3
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17
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36248937214
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note
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4, filtered and concentrated. The resulting oil was then charged on top of a column and purified by flash chromatography with a 8:2 hexane:AcOEt mixture followed by 7:3 hexane:AcOEt mixture as eluant.
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18
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36248952195
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note
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5: C, 65.27; H, 6.78; N, 7.25. Found: C, 65.31; H, 6.76; N, 7.23%.
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19
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36248940791
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note
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The reaction afforded always product 4 with the same diastereisomeric ratio (65/35) that was shown to be independent from the experimental conditions employed.
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21
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27144524535
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For recent examples of reactions catalysed by ScTDS, see:
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For recent examples of reactions catalysed by ScTDS, see:. Azoulay S., Manabe K., and Kobayashi S. Org. Lett. 7 (2005) 4593
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(2005)
Org. Lett.
, vol.7
, pp. 4593
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Azoulay, S.1
Manabe, K.2
Kobayashi, S.3
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23
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36249028743
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note
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The use of 1 or 2 mol/eq of free 4-methoxy aniline in the condensation between silyl ketene acetal 1 (2 mol/eq) and imine 2 (1 mol/eq) did not improve the reaction yield and did not alter the diastereoisomeric ratio of product 4.
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24
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36249008595
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note
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3: C, 73.82; H, 6.71; N, 7.17. Found: C, 73.79; H, 6.72; N, 7.19%.
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25
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36248987293
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note
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The reaction afforded always product 9 with the same diastereisomeric ratio (70/30) that was shown to be independent from the experimental conditions employed.
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26
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0034596298
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Recovery and recycling of scandium tris(dodecyl sulfate) have not been clearly accomplished:
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Recovery and recycling of scandium tris(dodecyl sulfate) have not been clearly accomplished:. Manabe K., Mori Y., Wakabayashi T., Nagayama S., and Kobayashi S. J. Am. Chem. Soc. 122 (2000) 7202
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(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 7202
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Manabe, K.1
Mori, Y.2
Wakabayashi, T.3
Nagayama, S.4
Kobayashi, S.5
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27
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0034602986
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For an example of recycle of supported scandium catalyst, see:
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For an example of recycle of supported scandium catalyst, see:. Nagayama S., and Kobayashi S. Angew. Chem., Int. Ed. 39 (2000) 567
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(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 567
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Nagayama, S.1
Kobayashi, S.2
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28
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36249007505
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note
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2O, DCM, AcOEt, or hexanes/AcOEt mixtures.
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30
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0036330875
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For examples of organocatalysed reactions carried out under the continuous flow mode, see:
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For examples of organocatalysed reactions carried out under the continuous flow mode, see:. Ishiara K., Hasegawa A., and Yamamoto H. Synlett (2002) 1296
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(2002)
Synlett
, pp. 1296
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Ishiara, K.1
Hasegawa, A.2
Yamamoto, H.3
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32
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36248975600
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note
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Procedure for catalyst recycling: SKTA 1 was reacted with imine 7 as described in note [10]. After 48 h 0.085 g of SKTA 1 and 0.124 g of imine 7 were added to the aqueous phase and a second reaction allowed to proceed for 48 h. After three further iterations of this procedure (for a total five reaction cycles) amide 9 was isolated after silica gel chromatography in 31% yield along with 10% β-lactams 8c and 8t as described above.
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34
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0032516375
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Annunziata R., Benaglia M., Cinquini M., Cozzi F., and Raimondi L. Tetrahedron Lett. 39 (1998) 3333
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(1998)
Tetrahedron Lett.
, vol.39
, pp. 3333
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Annunziata, R.1
Benaglia, M.2
Cinquini, M.3
Cozzi, F.4
Raimondi, L.5
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