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1
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15644378136
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For excellent reviews on the chemistry of electrophilic cyclopropanes, see: a
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For excellent reviews on the chemistry of electrophilic cyclopropanes, see: (a) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165.
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(1989)
Chem. Rev
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, pp. 165
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Wong, H.N.C.1
Hon, M.-Y.2
Tse, C.-W.3
Yip, Y.-C.4
Tanko, J.5
Hudlicky, T.6
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3
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51549121546
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For some recent examples, see: a
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For some recent examples, see: (a) Lifchits, O.; Alberico, D.; Zakharian, I.; Charette, A. B. J. Org. Chem. 2008, 73, 6838.
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(2008)
J. Org. Chem
, vol.73
, pp. 6838
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Lifchits, O.1
Alberico, D.2
Zakharian, I.3
Charette, A.B.4
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6
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46949091089
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For some recent examples, see: a
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For some recent examples, see: (a) Pohlhaus, P. D.; Sanders, S. D.; Parsons, A. T.; Li, W.; Johnson, J. S. J. Am. Chem. Soc. 2008, 130, 8642.
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(2008)
J. Am. Chem. Soc
, vol.130
, pp. 8642
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Pohlhaus, P.D.1
Sanders, S.D.2
Parsons, A.T.3
Li, W.4
Johnson, J.S.5
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7
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41149174128
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(b) Jackson, S. K.; Karadeolian, A.; Driega, A. B.; Kerr, M. A. J. Am. Chem. Soc. 2008, 130, 4196.
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(2008)
J. Am. Chem. Soc
, vol.130
, pp. 4196
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Jackson, S.K.1
Karadeolian, A.2
Driega, A.B.3
Kerr, M.A.4
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8
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34547812232
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(c) Bajtos, B.; Yu, M.; Zhao, H.; Pagenkopf, B. L. J. Am. Chem. Soc. 2007, 129, 9631.
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(2007)
J. Am. Chem. Soc
, vol.129
, pp. 9631
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Bajtos, B.1
Yu, M.2
Zhao, H.3
Pagenkopf, B.L.4
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9
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46949106418
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(d) Perreault, C.; Goudreau, S. R.; Zimmer, L. E.; Charette, A. B. Org. Lett. 2008, 10, 689.
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(2008)
Org. Lett
, vol.10
, pp. 689
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Perreault, C.1
Goudreau, S.R.2
Zimmer, L.E.3
Charette, A.B.4
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11
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0041806585
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(f) Young, I. S.; Kerr, M. A. Angew. Chem., Int. Ed. 2003, 42, 3023.
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Angew. Chem., Int. Ed
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, pp. 3023
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Young, I.S.1
Kerr, M.A.2
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13
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0038222536
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(b) Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
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(2003)
Chem. Rev
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Lebel, H.1
Marcoux, J.-F.2
Molinaro, C.3
Charette, A.B.4
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14
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33744462643
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For examples of cyclopropanations using iodonium ylides, see: (a) Müller, P; Allenbach, Y. F, Chappelet, S, Ghanem, A. Synthesis 2006, 1689
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For examples of cyclopropanations using iodonium ylides, see: (a) Müller, P; Allenbach, Y. F.; Chappelet, S.; Ghanem, A. Synthesis 2006, 1689.
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17
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15044355865
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(d) Ghanem, A.; Lacrampe, F.; Schuring, V. Helv. Chim. Acta 2005, 88, 216.
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(2005)
Helv. Chim. Acta
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Ghanem, A.1
Lacrampe, F.2
Schuring, V.3
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21
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0037418813
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(h) Müller, P.; Allenbach, Y.; Robert, E. Tetrahedron: Asymmetry 2003, 14, 779.
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(2003)
Tetrahedron: Asymmetry
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, pp. 779
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Müller, P.1
Allenbach, Y.2
Robert, E.3
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24
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0037136119
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(k) Batsila, C.; Kostakis, G.; Hadjiarapoglou, L. P. Tetrahedron Lett. 2002, 43, 5997.
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(2002)
Tetrahedron Lett
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, pp. 5997
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Batsila, C.1
Kostakis, G.2
Hadjiarapoglou, L.P.3
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27
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58149300310
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(n) Dauban, P.; Saniere, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 20, 5189.
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(2001)
J. Am. Chem. Soc
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, pp. 5189
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Dauban, P.1
Saniere, L.2
Tarrade, A.3
Dodd, R.H.4
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29
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85033148217
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and references cited therein
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(p) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431, and references cited therein.
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(1990)
Synthesis
, pp. 431
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Moriarty, R.M.1
Vaid, R.K.2
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30
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53849087842
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González-Bobes, F.; Fenster, M. D. B.; Kiau, S.; Kolla, L.; Kolotuchin, S.; Soumeillant, M. Adv. Synth. Catal. 2008, 350, 813.
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(2008)
Adv. Synth. Catal
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, pp. 813
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González-Bobes, F.1
Fenster, M.D.B.2
Kiau, S.3
Kolla, L.4
Kolotuchin, S.5
Soumeillant, M.6
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32
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0034738043
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Camacho, M. B.; Clark, A. E.; Liebrecht, T. A.; DeLuca, J. P. J. Am. Chem. Soc. 2000, 122, 5210.
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(2000)
J. Am. Chem. Soc
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, pp. 5210
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Camacho, M.B.1
Clark, A.E.2
Liebrecht, T.A.3
DeLuca, J.P.4
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33
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45249087416
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(a) Moriarty, R. M.; Tyagi, S.; Ivanov, D.; Constantinescu, M, J. Am. Chem. Soc. 2008, 130, 7564.
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(2008)
J. Am. Chem. Soc
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, pp. 7564
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Moriarty, R.M.1
Tyagi, S.2
Ivanov, D.3
Constantinescu, M.4
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34
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44449160072
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(b) Huang, X.-C.; Liu, Y.-L.; Liang, Y.; Pi, S.-F.; Wang, F.; Li, J.-H. Org. Lett. 2008, 10, 1525.
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(2008)
Org. Lett
, vol.10
, pp. 1525
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Huang, X.-C.1
Liu, Y.-L.2
Liang, Y.3
Pi, S.-F.4
Wang, F.5
Li, J.-H.6
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36
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0242491841
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(d) Adam, W.; Gogonas, E. P.; Hadjiarapoglou, L. P. J. Org. Chem. 2003, 68, 9155.
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J. Org. Chem
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Adam, W.1
Gogonas, E.P.2
Hadjiarapoglou, L.P.3
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37
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3242710296
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(e) Müller, P.; Allenbach, Y. F.; Ferri, M.; Bernardinelli, G. ARKIVOC 2003, 7, 80.
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(2003)
ARKIVOC
, vol.7
, pp. 80
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Müller, P.1
Allenbach, Y.F.2
Ferri, M.3
Bernardinelli, G.4
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40
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58149308894
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(h) Viktor, V.; Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2565.
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(2002)
Chem. Rev
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Viktor, V.1
Zhdankin, V.V.2
Stang, P.J.3
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44
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58149294089
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Concentration at higher temperature gave significantly lower yields
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Concentration at higher temperature gave significantly lower yields.
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45
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58149280904
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Since these side products are generally formed in the subsequent reaction, they do not interfere in the cyclopropanation reaction. Indeed, no significant difference in the yields were observed in cyclopropanation when the crude ylide was used
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Since these side products are generally formed in the subsequent reaction, they do not interfere in the cyclopropanation reaction. Indeed, no significant difference in the yields were observed in cyclopropanation when the crude ylide was used.
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46
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58149314634
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See Supporting Information
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See Supporting Information.
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47
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58149296616
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The iodonium ylide of the Meldrum's acid is an exception since it is stable at room temperature for many weeks
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The iodonium ylide of the Meldrum's acid is an exception since it is stable at room temperature for many weeks
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48
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58149288724
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Müller and Hadjiarapoglou have reported the synthesis of this iodonium ylide in 56 and 61% yield respectively (see refs 5f and 5o).
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Müller and Hadjiarapoglou have reported the synthesis of this iodonium ylide in 56 and 61% yield respectively (see refs 5f and 5o).
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49
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58149290302
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Five percent yield was obtained when MgO was added
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Five percent yield was obtained when MgO was added.
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50
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0025073109
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Lee, E.; Jung, K. W.; Kim, Y. S. Tetrahedron Lett. 1990, 31, 1023.
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(1990)
Tetrahedron Lett
, vol.31
, pp. 1023
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Lee, E.1
Jung, K.W.2
Kim, Y.S.3
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51
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58149280905
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6 complex was used.
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6 complex was used.
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52
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58149288725
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esp = α,α,α′,α′-Tetramethyl-1,3- benzenedipropanoate.
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esp = α,α,α′,α′-Tetramethyl-1,3- benzenedipropanoate.
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