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1
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0038222536
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A review of stereoselective cyclopropanations: Lebel, H.; Marcoux, J.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
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A review of stereoselective cyclopropanations: Lebel, H.; Marcoux, J.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
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3
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0032482059
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For selected recent examples with high ee, see Simmons-Smith type: (a) Denmark, S. E.; O'Connor, S. P.; Wilson, S. R. Angew. Chem., Int. Ed. 1998, 37, 1149.
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For selected recent examples with high ee, see Simmons-Smith type: (a) Denmark, S. E.; O'Connor, S. P.; Wilson, S. R. Angew. Chem., Int. Ed. 1998, 37, 1149.
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4
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0035852090
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and references therein
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(b) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168 and references therein.
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J. Am. Chem. Soc
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Charette, A.B.1
Molinaro, C.2
Brochu, C.3
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5
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85008090337
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Metallocarbenoid-mediated reaction: (c) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726.
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Metallocarbenoid-mediated reaction: (c) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726.
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6
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0000139463
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(d) Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S.-B.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223.
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J. Am. Chem. Soc
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Nishiyama, H.1
Itoh, Y.2
Matsumoto, H.3
Park, S.-B.4
Itoh, K.5
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7
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0029945485
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(e) Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.; Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6897.
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(1996)
J. Am. Chem. Soc
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Davies, H.M.L.1
Bruzinski, P.R.2
Lake, D.H.3
Kong, N.4
Fall, M.J.5
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8
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34250726079
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3889 and references therein. For other examples, see a review in
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(f) Kanchiku, S.; Suematsu, H.; Matsumoto, K.; Uchida, T.; Katsuki, T. Angew. Chem., Int. Ed. 2007, 46, 3889 and references therein. For other examples, see a review in ref 1.
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Angew. Chem., Int. Ed
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Kanchiku, S.1
Suematsu, H.2
Matsumoto, K.3
Uchida, T.4
Katsuki, T.5
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9
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0035901642
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Catalytic generation of chiral ylides: (a) Aggarwal, V. K.; Alonso, E.; Fang, G. Y.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433 and references therein.
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Catalytic generation of chiral ylides: (a) Aggarwal, V. K.; Alonso, E.; Fang, G. Y.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433 and references therein.
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10
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5344280509
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(b) Papageorgiou, C. D.; Cubillo de Dios, M. A.; Ley, S. V.; Gaunt, M. J. Angew. Chem., Int. Ed. 2004, 43, 4641.
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(2004)
Angew. Chem., Int. Ed
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Papageorgiou, C.D.1
Cubillo de Dios, M.A.2
Ley, S.V.3
Gaunt, M.J.4
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11
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14944346768
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Catalytic activation of electrophiles: (a) Kunz R. K.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 3240.
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Catalytic activation of electrophiles: (a) Kunz R. K.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 3240.
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12
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34547098110
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For similar works, b
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For similar works, (b) Hartikka, A.; Arvidsson, P. I. J. Org. Chem. 2007, 72, 5874.
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(2007)
J. Org. Chem
, vol.72
, pp. 5874
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Hartikka, A.1
Arvidsson, P.I.2
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13
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34447526191
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(c) Hartikka, A.; Slósarczyka, A. T.; Arvidsson, P. I. Tetrahedron: Asymmetry 2007, 18, 1403.
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(2007)
Tetrahedron: Asymmetry
, vol.18
, pp. 1403
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Hartikka, A.1
Slósarczyka, A.T.2
Arvidsson, P.I.3
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14
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0033612173
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For other organocatalytic approach, see also (a) Arai, S.; Nakayama, K.; Ishida, T.; Shioiri, T. Tetrahedron Lett. 1999, 40, 4215.
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For other organocatalytic approach, see also (a) Arai, S.; Nakayama, K.; Ishida, T.; Shioiri, T. Tetrahedron Lett. 1999, 40, 4215.
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15
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34447533890
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(b) Rios, R.; Sundén, H.; Vesely, J.; Zhao, G.-L.; Dziedzic, P.; Córdova, A. Adv. Synth. Catal. 2007, 349, 1028.
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(2007)
Adv. Synth. Catal
, vol.349
, pp. 1028
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Rios, R.1
Sundén, H.2
Vesely, J.3
Zhao, G.-L.4
Dziedzic, P.5
Córdova, A.6
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16
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34848814187
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(c) Xie, H.; Zu, L.; Li, H.; Wang, J.; Wang, W. J. Am. Chem. Soc. 2007, 129, 10886.
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(2007)
J. Am. Chem. Soc
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, pp. 10886
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Xie, H.1
Zu, L.2
Li, H.3
Wang, J.4
Wang, W.5
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17
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0034684524
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With stoichiometric amount of Lewis acids and a chiral ligand: Mamai, A, Madalengoitia, J. S. Tetrahedron Lett. 2000, 41, 9009
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With stoichiometric amount of Lewis acids and a chiral ligand: Mamai, A.; Madalengoitia, J. S. Tetrahedron Lett. 2000, 41, 9009.
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18
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0036625219
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Review of heterobimetallic rare earth-alkali metal-BINOL complexes: Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187.
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Review of heterobimetallic rare earth-alkali metal-BINOL complexes: Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187.
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19
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0008757162
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2: (a) Harada, T.; Tuyet, T. M. T.; Oku, A. Org. Lett. 2000, 2, 1319.
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2: (a) Harada, T.; Tuyet, T. M. T.; Oku, A. Org. Lett. 2000, 2, 1319.
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20
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34248189099
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Utility of biphenyldiols as rare earth metal complexes: (b) Kakei, H.; Tsuji, R.; Ohshima, T.; Morimoto, H.; Matsunaga, S.; Shibasaki, M. Chem. Asian J. 2007, 2, 257 and references therein.
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Utility of biphenyldiols as rare earth metal complexes: (b) Kakei, H.; Tsuji, R.; Ohshima, T.; Morimoto, H.; Matsunaga, S.; Shibasaki, M. Chem. Asian J. 2007, 2, 257 and references therein.
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21
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33748496246
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(c) Tosaki, S.-y.; Hara, K.; Gnanadesikan, V.; Morimoto, H.; Harada, S.; Sugita, M.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 11776.
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(2006)
J. Am. Chem. Soc
, vol.128
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Tosaki, S.-Y.1
Hara, K.2
Gnanadesikan, V.3
Morimoto, H.4
Harada, S.5
Sugita, M.6
Yamagiwa, N.7
Matsunaga, S.8
Shibasaki, M.9
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22
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34548154771
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Use as alkaline earth metal complex: (d) Yamaguchi, A.; Aoyama, N.; Matsunaga, S.; Shibasaki, M. Org. Lett. 2007, 9, 3387.
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Use as alkaline earth metal complex: (d) Yamaguchi, A.; Aoyama, N.; Matsunaga, S.; Shibasaki, M. Org. Lett. 2007, 9, 3387.
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23
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2942635094
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Utility of α,β-unsaturated N-acylpyrrole as an ester surrogate: Matsunaga, S.; Kinoshita, T.; Okada, S.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 7559 and references therein.
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Utility of α,β-unsaturated N-acylpyrrole as an ester surrogate: Matsunaga, S.; Kinoshita, T.; Okada, S.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 7559 and references therein.
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24
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35948949422
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For more detailed results and discussion of the NaI and LiI effects, see Supporting Information
-
For more detailed results and discussion of the NaI and LiI effects, see Supporting Information.
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25
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35948958136
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+ were observed (see Supporting Information).
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+ were observed (see Supporting Information).
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26
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35948988444
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- would not be so important in this system.
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- would not be so important in this system.
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27
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11944252146
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3 complex in asymmetric 1,4-addition reaction.(a) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194.
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3 complex in asymmetric 1,4-addition reaction.(a) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194.
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28
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34548159259
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For recent studies on the effects of alkali metals, see: (b) Wooten, A. J.; Carroll, P. J.; Walsh, P. J. Org. Lett. 2007, 9, 3359. See also, a review in ref 8.
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For recent studies on the effects of alkali metals, see: (b) Wooten, A. J.; Carroll, P. J.; Walsh, P. J. Org. Lett. 2007, 9, 3359. See also, a review in ref 8.
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29
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85215328951
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For structural analysis of heterobimetallic rare earth-alkali metal-BINOL complexes, see a review in ref 7. See also: (a) Aspinall, H. C.; Bickley, J. F.; Dwyer, J. L. M.; Greeves, N.; Kelly, R. V.; Steiner, A. Organometallics 2000, 19, 5416.
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For structural analysis of heterobimetallic rare earth-alkali metal-BINOL complexes, see a review in ref 7. See also: (a) Aspinall, H. C.; Bickley, J. F.; Dwyer, J. L. M.; Greeves, N.; Kelly, R. V.; Steiner, A. Organometallics 2000, 19, 5416.
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33746294798
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(b) Wooten, A. J.; Carroll, P. J.; Walsh, P. J. Angew. Chem., Int. Ed. 2006, 45, 2549.
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(2006)
Angew. Chem., Int. Ed
, vol.45
, pp. 2549
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Wooten, A.J.1
Carroll, P.J.2
Walsh, P.J.3
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(c) Di Bari, L.; Lelli, M.; Pintacuda, G.; Pescitelli, G.; Marchetti, F.; Salvadori, P. J. Am. Chem. Soc. 2003, 125, 5549.
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(2003)
J. Am. Chem. Soc
, vol.125
, pp. 5549
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Di Bari, L.1
Lelli, M.2
Pintacuda, G.3
Pescitelli, G.4
Marchetti, F.5
Salvadori, P.6
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32
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25444512653
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Although any proposed reaction mechanism is speculative at present, there are two possibilities. One is simple Lewis acid-accelerated mechanism, and the other mechanism is dual control of both enone 3 and ylide 2 by the La-Li3-(1b)3, NaI complex. Similar dual control mechanism is proposed by MacMillan see ref 5a, Interaction of ylide 2 with catalyst might be operative through oxygen atom of ylide 2 in the latter case. Mechanistic aspects of the present reaction will be reported in due course as a full article. We proposed related dual control mechanism in aza-Michael reaction of alkoxylamines: Yamagiwa, N, Qin, H, Matsunaga, S, Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 13419
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3 + NaI complex. Similar dual control mechanism is proposed by MacMillan (see ref 5a). Interaction of ylide 2 with catalyst might be operative through oxygen atom of ylide 2 in the latter case. Mechanistic aspects of the present reaction will be reported in due course as a full article. We proposed related dual control mechanism in aza-Michael reaction of alkoxylamines: Yamagiwa, N.; Qin, H.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 13419.
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